[ CAS No. 6276-54-6 ] {[proInfo.proName]}

Name: 6276-54-6|3-Chloropropan-1-amine hydrochloride|98%
Brand: Ambeed
SKU: A257632
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2D 3D

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Quality Control of [ 6276-54-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6276-54-6 ]

Product Details of [ 6276-54-6 ]

CAS No. :	6276-54-6	MDL No. :	MFCD00012913
Formula :	C₃H₉Cl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	130.02	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 6276-54-6 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.0
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.03
Log Po/w (WLOGP) :	1.38
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	0.51
Consensus Log Po/w :	0.81

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.16
Solubility :	8.93 mg/ml ; 0.0687 mol/l
Class :	Very soluble
Log S (Ali) :	-1.17
Solubility :	8.86 mg/ml ; 0.0682 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.26
Solubility :	7.14 mg/ml ; 0.055 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.29

Safety of [ 6276-54-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6276-54-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 6276-54-6 ]
Downstream synthetic route of [ 6276-54-6 ]

[ 6276-54-6 ] Synthesis Path-Upstream 1~3

1
[ 110-91-8 ]
[ 6276-54-6 ]
[ 123-00-2 ]

Reference： [1] Patent: CN107619390, 2018, A, . Location in patent: Paragraph 0015

2
[ 156-87-6 ]
[ 6276-54-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With thionyl chloride In chloroform at 0℃; Reflux	To solution of thionyl chloride (8.68 g, 1.32 mmol) in anhydrous chloroform (30 mL) was added dropwise to 3-aminopropan-l-ol (4.49 g, 59.19 mmol) while maintaining the temperature at 0 - 10 °C. The mixture was allowed to warm to room temperature and then heated at reflux for 3 h. The mixture was cooled to room temperature and the precipitate was collected to give 3-chloropropylamine hydrochloride (8A) (7.07 g, 55.15 mmol, 93percent) as a green solid. ESMS m/z 94 (M+H)⁺.
93%	With thionyl chloride In chloroform at 0 - 20℃; for 3 h; Reflux	Step 1: Synthesis of 3-chloropropylamine hydrochloride (8)[00261j To solution of thionyl chloride (8.68 g, 1.32 mmol) in anhydrous chloroform (30 mL) was added dropwise to 3-aminopropan-1-ol (4.49 g, 59.19 mmol) while maintaining the temperature at 0 — 10 °C. The mixture was allowed to warm to room temperature and then heated at reflux for 3 h. The mixture was cooled to room temperature and the precipitate was collected to give 3-chloropropylamine hydrochloride (8) (7.07 g, 55.15 mmol, 93percent) as a green solid. ESMS mlz 94 (M+H).

Reference： [1] Patent: WO2014/18571, 2014, A2, . Location in patent: Paragraph 00463
[2] Patent: WO2014/18570, 2014, A1, . Location in patent: Paragraph 00261
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5413 - 5417[4] Angew. Chem., 2018, vol. 130, p. 5511 - 5515,5

3
[ 50-00-0 ]
[ 6276-54-6 ]
[ 5407-04-5 ]

Reference： [1] Journal of the Chemical Society. Dalton Transactions, 2001, # 8, p. 1306 - 1318

[ 6276-54-6 ] Synthesis Path-Downstream 1~29

1
[ 109-06-8 ]
[ 6276-54-6 ]
[ 34974-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; sodium amide Yield given. Multistep reaction;

Reference： [1]Cooper; Durant; Ganellin; Ife; Meeson; Sach [Il Farmaco, 1991, vol. 46, # 1, p. 3 - 19]

2
[ 583-61-9 ]
[ 6276-54-6 ]
[ 88596-90-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium amide; In ammonia;	(a) <strong>[583-61-9]2,3-Lutidine</strong> (321 g) was added with stirring to a solution of sodamide (351 g) in liquid ammonia (3 l). 1-Amino-3-chloropropane hydrochloride (429 g) was added to this mixture over 8 minutes with stirring. Any liquid ammonia lost through evaporation was replaced. After 2 hours the reaction was quenched by the addition of ammonium chloride (120 g) and the reaction mixture was left to stand overnight to allow substantially complete escape of ammonia through evaporation. The residue so obtained was diluted with water (2 l) and extracted with dichloromethane. The extracts were dried (Na2 SO4), the dichloromethane removed by evaporation and the residue distilled in vacuo to give 4-(3-methyl-2-pyridyl)butylamine (306.6 g).
	With sodium amide; In ammonia;	EXAMPLE 2 <strong>[583-61-9]2,3-Lutidine</strong> (321 g) was added with stirring to a solution of sodamide (351 g) in liquid ammonia (3 1). 1-Amino-3-chloropropane hydrochloride (429g) was added to this mixture over 8 minutes with stirring. Any liquid ammonia lost through evaporation was replaced. After 2 hours the reaction was quenched by the addition of ammonium chloride (120 g) and the reaction mixture was left to stand overnight to allow substantially complete escape of ammonia through evaporation. The residue so obtained was diluted with water (2 1) and extracted with dichloromethane. The extracts were dried (Na2 SO4), the dichloromethane removed by evaporation and the residue distilled in vacuo to give 4-(3-methyl-2-pyridyl) butylamine (306.6 g).

Reference： [1]Il Farmaco,1991,vol. 46,p. 3 - 19
[2]Patent: US4515952,1985,A
[3]Patent: US4526974,1985,A

3
[ 10500-57-9 ]
[ 6276-54-6 ]
[ 112668-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; sodium amide 2) 2 h; Yield given. Multistep reaction;
	With sodium amide In ammonia	1.a 2-[3-(5,6,7,8-Tetrahydroquinol-8-yl)propylamino]-5-[1-oxopyrid-4-ylmethyl]-4(1H)-pyrimidone (a) 5,6,7,8-Tetrahydroquinoline (20 g) was added quickly to sodamide (17.6 g) in liquid ammonia (250 ml) to give a dark red coloured solution. 3-Chloropropylamine hydrochloride (28.9 g) was added in portions over four hours when loss of colour was permanent after which the reaction was stirred for a further 2 hours and then quenched with ammonium chloride (20 g). The liquid ammonia was allowed to evaporate and the residues were partitioned between chloroform and water. The pH was lowered to 6 and the chloroform layer was discarded. The aqueous layer was basified (pH 12-14), and extracted with chloroform, the chloroform extracts were dried, combined, evaporated and the residue was vacuum distilled to give 3-(5,6,7,8-tetrahydroquinol-8-yl)propylamine (7.58 g), b.p. 92°-94° C. at 0.1 mm Hg.
	With sodium amide In ammonia	2.a EXAMPLE 2 (a) 5,6,7,8-Tetrahydroquinoline (20 g) was added quickly to sodamide (17.6 g) in liquid ammonia (250 ml) to give a dark red coloured solution. 3-Chloropropylamine hydrochloride (28.9 g) was added in portions over four hours when loss of colour was permanent after which the reaction was stirred for a further 2 hours and then quenched with ammonium chloride (20 g). The liquid ammonia was allowed to evaporate and the residues were partitioned between chloroform and water. The pH was lowered to 6 and the chloroform layer was discarded. The aqueous layer was basified (pH 12-14), and extracted with chloroform, the chloroform extracts were dried, combined, evaporated and the residue was vacuum distilled to give 3-(5,6,7,8-tetrahydroquinol-8-yl) propylamine (7.58 g), b.p. 92°-94° C. at 0.1 mm Hg.

Reference： [1]Cooper; Durant; Ganellin; Ife; Meeson; Sach [Il Farmaco, 1991, vol. 46, # 1, p. 3 - 19]
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4727076, 1988, A
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4764519, 1988, A

4
[ 24424-99-5 ]
[ 6276-54-6 ]
[ 116861-31-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In chloroform; at 20℃;	Example 1 The Synthesis of Compound (8)wherein [0094] Under stirring, a solution of di-tert-butyl di-carbonate (23.79 g, 110 mmol) in chloroform (50 mL) is slowly added into a solution of 3-chloropropylamine hydrochloride (11.0 g, 110 mmol) and triethylamine (18.42 mL, 130 mmol) in chloroform (50 mL). After stirring overnight at room temperature, a brown oil is obtained as a crude product. Then compound (8-2) (22 g, 95%) as a colorless solid is produced by Kugelrohr distillation at a temperatures of less than 48 C.
94%	With sodium hydroxide; In tetrahydrofuran; water; at 0℃;	Preparation of Compound 1aDi-tert-butyl-dicarbonate (0.228 g, 1.04 mmol) and sodium hydroxide (0.096 g, 2.4 mmol) were added to a cooled solution of 3-chloropropan-1-amine (0.15 g, 1.04 mmol) in water (10 ml) and THF (10 ml). The resulting mixture was stirred overnight at 0 C. The aqueous layer was then extracted with ethyl acetate (10 ml×4). The combined organic layer was washed with brine (25 ml), dried over sodium sulfate and concentrated. The residue was then purified by column chromatography on silica gel to afford 0.306 g of colorless oil. Yield: 94.0%. 1H NMR (300 MHz, CDCl3) delta1.39 (s, 9H), 81.91 (m, 2H), 83.23 (m, 2H), delta3.53 (t, J=6.4 Hz, 2H), 64.89 (s, 1H). 13C NMR (75 MHz, CDCl3) delta (ppm): 156.0, 79.2, 42.3, 37.9, 32.6, 28.3. MS (ESI): m/z calcd for C8H16ClNO2 193.09, found 193.52 [M+H]+
93%	With triethylamine; In chloroform; at 0℃; for 1h;Inert atmosphere; Reflux;	General procedure: A reaction flask was charged with chloroethylamine hydochloride 48a (1.00 g, 8.62 mmol), di-tert-butyl dicarbonate (1.88 g, 8.62 mmol) and CHCl3 (50 mL) under argon atmosphere. To a mixture is added triethylamine (0.91 g, 9.05 mmol) slowly at 0 C, and the mixture was heated under reflux for 1h. After washing the reaction mixture with water, the volatile materials were removed under reduced pressure. The crude residue was purified by silica gel column chromatography (CHCl3/MeOH=8:2) to yield 49a (95 %). The 49b was prepared in a 93% yield by a similar method starting with 48b.

83.7%		An aqueous sodium dicarbonate solution (3.5 g in 57 ml of water) and solid sodium chloride (7.5 g) were added at 0 C. to a suspension of 3-chloropropylamine hydrochloride (38 mmol) in DCM (77 ml), and the mixture was stirred for 30 minutes. A solution of Boc anhydride (1.2 eq.) in dichloromethane (20 ml) was then slowly added dropwise. The reaction mixture was stirred overnight at RT. The reaction mixture was extracted with dichloromethane, and the org. phase was washed with water and sat. sodium chloride solution, dried over sodium sulfate (anhydrous) and concentrated. The desired product was used in the next stage without being purified further.Yield: 83.7%
82%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 5h;Inert atmosphere;	3-chloropropylamine-HCL (5 g, 38.46 mmole, 1.0 equiv) was dissolved in 20 mL dry DCM under inert atmosphere. DIPEA (5.47g , 42.31 mmole, 1.1 equiv) was added via syringe at room temperature to the stirring mixture. When the solution was clear and all reagents solubilized, the reaction mixture was cooled to 00C. Under inert atmosphere, boc-anhydride (8.4 g, 38.49 mmole, 1.1 equiv) was dissolved in 5 mL dry DCM. This solution was added slowly to the stirring solution of 3-chloropropylamine-HCL at 00C. After addition, the solution was allowed to warm up to R.T. and mix for 5 hrs while monitoring for completion by TLC and LC/MS. Upon completion, 25 mL of H2O was added to the reaction at ambient atmosphere while mixing. The mixture was then diluted, transferred to a seperatory funnel, and the water layer extracted into DCM (3 x 20 mL). The organic layer was dried over Na2SO4, filtered, and evaporated to dryness to afford a crude powder. The product was purified by Hex: EtOAc silica chromatography using a CombiFlash purification system. Product eluted at 2 : 1 Hex: EtOAc and collected fractions were evaporated to dryness to afford S1-1 as a white powder (MW: 193.67 g/mol, 6.08 g, 82% yield).1H NMR (400 MHz, CDCl3): 3.58 (t, J = 6.4 Hz, 2H), 3.27 (m, 2H), 1.96 (m, 2H), 1.43 (s, 9H).
68%	With sodium hydroxide; In tetrahydrofuran; at 0℃;	di-tert-butyl dicarbonate(10.89 g, 50mmol)was dissolved in 50 ml THF. The solutionwas cooledto 0 C. 3-Chloropropan-1-amine hydrochloride (6.46 g, 69 mmol) wasdissolved in 20 ml of 1 M NaOH solution and added using a droppingfunnel, and the solution was stirred overnight. 150 ml of ethyl acetatewere added and extraction was performed. The organic phase waswashed three times with water and once with brine, and then driedover magnesium sulfate. The solvent was removed and a viscous oilwas produced, which was dried under vacuum (7.27 g, 68%). 1H NMR(400 MHz, CDCl3) delta (ppm): 4.80 (bs, NH), 3.53 (t, J = 6.4 Hz, 2H),3.22 (q, J = 6.4 Hz, 2H), 1.91 (quin, J = 6.4 Hz, 2H),1.42 (s, 9 H). 13CNMR (100 MHz, CDCl3, delta, ppm): 156, 79, 42, 37, 32, 28.
7.89 g		A mixture of 3-chloropropylamine hydrochloride (8A) (5.00 g, 38.46 mmol) and triethylamine (4.11 g, 40.58 mmol) in dichloromethane was stirred at room temperature for 30 min. The mixture was cooled to 0 C and a solution of di-terz-butyl dicarbonate (8.86 g, 40.58 mmol) in dichloromethane (30 mL) was added. The mixture was stirred at room temperature for 2 h. The reaction mixture was washed with 10% aqueous potassium hydrogen sulfate (40 mL) and water (40 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to give tert-butyl 3-chloropropylcarbamate (9A) (7.89 g, 40.77 mmol, quantitative) as a light brown oil. The crude material was used in the next step without further purification. ESMS m/z 138 (M+H - r-Bu)+.
		Step 2: Synthesis of tert-butyl 3-chloropropylcarbamate (9)[00262j A mixture of 3-chloropropylamine hydrochloride (8) (5.00 g, 38.46 mmol) and triethylamine (4.11 g, 40.58 mmol) in dichloromethane was stirred at room temperature for 30 mm. The mixture was cooled to 0 C and a solution of di-tert-butyl dicarbonate (8.86 g, 40.58 mmol) in dichloromethane (30 mL) was added. The mixture was stirred at room temperature for 2 h. The reaction mixture was washed with 10% aqueous potassium hydrogen sulfate (40 mL) and water (40 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to give tert-butyl 3 -chloropropylcarbamate (9) (7.89 g, 40.77 mmol, quantitative) as a light brown oil. The crude material was used in the next step without further purification. ESMS mlz 138 (M+H - t-Bu).

Reference： [1]Organic Preparations and Procedures International,1996,vol. 28,p. 65 - 76
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 1458 - 1462
Angew. Chem.,2019,vol. 131,p. 1472 - 1476,5
[3]Tetrahedron,2000,vol. 56,p. 4759 - 4764
[4]Patent: US2013/178470,2013,A1 .Location in patent: Paragraph 0094
[5]Patent: US2012/288884,2012,A1 .Location in patent: Page/Page column 9
[6]European Journal of Medicinal Chemistry,2014,vol. 82,p. 16 - 35
[7]Steroids,2002,vol. 67,p. 71 - 75
[8]Helvetica Chimica Acta,1993,vol. 76,p. 1636 - 1648
[9]Tetrahedron,1998,vol. 54,p. 15199 - 15214
[10]Chemical Communications,2007,p. 4647 - 4649
[11]Journal of the American Chemical Society,2011,vol. 133,p. 14208 - 14211
[12]Journal of Polymer Science, Part A: Polymer Chemistry,2010,vol. 48,p. 2044 - 2052
[13]Patent: US2010/222324,2010,A1 .Location in patent: Page/Page column 59-60
[14]Chemical Communications,2012,vol. 48,p. 6833 - 6835
[15]Patent: WO2018/112420,2018,A1 .Location in patent: Paragraph 0734; 0735
[16]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 565 - 570
[17]Reactive and functional polymers,2015,vol. 96,p. 32 - 38
[18]Journal of the American Chemical Society,1996,vol. 118,p. 715 - 721
[19]Tetrahedron Letters,2000,vol. 41,p. 9691 - 9693
[20]Journal of the American Chemical Society,2012,vol. 134,p. 769 - 772
[21]Patent: WO2014/18571,2014,A2 .Location in patent: Paragraph 00464
[22]Patent: WO2014/18570,2014,A1 .Location in patent: Paragraph 00262

5
[ 6276-54-6 ]
[ 4376-01-6 ]
[ 16605-03-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	In tetrahydrofuran 1. -78 deg C, 2 h, 2. 60-70 deg C, 8 h, reflux;

Reference： [1]Kashiwabara, Kazuo; Jung, Minho; Fujita, Junnosuke [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 8, p. 2372 - 2377]

6
[ 73279-04-6 ]
[ 6276-54-6 ]
[ 73278-98-5 ]

Yield	Reaction Conditions	Operation in experiment
91.7%	With potassium iodide; sodium hydroxide; In dimethyl sulfoxide; at 100 - 110℃; for 20h;	Add 750 g of dimethyl sulfoxide to the reaction flask.420 g (2.196 mol) of compound 1 (prepared in Example 3) are added,Add 340g (8.5mol) of sodium hydroxide, heat, raise the temperature to about 90 °C, add 14g of potassium iodide,Under stirring, 340 g (2.615 mol) of 3-chloropropylamine hydrochloride was added in portions, and the reaction was incubated at 100-110° C. for 20 hr.After confirmation of the reaction, 1000 g of water was added, pH=10~11 was adjusted with concentrated hydrochloric acid, and the mixture was stirred for about 1.5 hr. The mixture was allowed to stand for liquid separation. The aqueous phase was extracted once with 800 g of toluene. The organic phase was combined and used 50 kg of sodium chloride. The aqueous solution was washed once, and the liquid was separated. The organic solvent was concentrated and the solvent was weighed to obtain 500 g of an oil (theoretical amount: 545.38 g). Yield: 91.7percent.

Reference： [1]Synthetic Communications,1999,vol. 29,p. 15 - 20
[2]Patent: CN107698538,2018,A .Location in patent: Paragraph 0067-0068

7
[ 6276-54-6 ]
[ 829-85-6 ]
[ 16605-03-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium <i>tert</i>-butylate In tetrahydrofuran for 20h; Heating;

Reference： [1]Habtemanam, Abraha; Watchman, Beth; Potter, Brian S.; Palmer, Rex; Parsons, Simon; Parkin, Andrew; Sadler, Peter J. [Journal of the Chemical Society. Dalton Transactions (2001), 2001, # 8, p. 1306 - 1318]

8
[ 5779-94-2 ]
[ 6276-54-6 ]
N-(3-chloropropyl)-(2,5-dimethylphenyl)methaneimine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate In water at 20℃;

Reference： [1]Yus; Soler; Foubelo [Journal of Organic Chemistry, 2001, vol. 66, # 18, p. 6207 - 6208]

9
[ 939-80-0 ]
[ 6276-54-6 ]
[ 475489-76-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2589 - 2596

10
[ 6276-54-6 ]
[ 1079-66-9 ]
[ 16605-03-1 ]
[ 19755-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: chloro-diphenylphosphine With sodium In tetrahydrofuran at 20℃; Stage #2: 3-chloropropylamine hydrochloride In tetrahydrofuran at 50℃; for 10h; Title compound not separated from byproducts;

Reference： [1]Koshti, Nirmal; Naik, Shubhangi; Parab, Bharat [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 4, p. 852 - 856]

11
[ 6276-54-6 ]
[ 29026-74-2 ]
[ 748771-92-8 ]

Yield	Reaction Conditions	Operation in experiment
15%	With triethylamine; In isopropyl alcohol; at 50 - 90℃; for 48h;	A. N1-(2-Isopropoxy-phenyl)-propane-1,3-diamine. To a solution of <strong>[29026-74-2]2-isopropoxy-phenylamine</strong> (0.50 g, 3.3 mmol) in isopropanol (7 mL) was added Et3N (0.67 g, 6.6 mmol) and 3-chloropropylamine hydrochloride (0.515 g, 3.96 mmol). The reaction mixture was heated to 50 C. for 24 h, then to 90 C. for 24 h. The mixture was treated with satd NaHCO3 (20 mL), EtOAc (40 mL) and H2O (20 mL), and then the aqueous layer was back-extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (50-100% EtOAc/hexanes) to provide an amber oil (0.10 g, 15%). MS (ESI): mass calculated for C12H20N2O, 208.16; m/z found, 209.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 6.85-6.81 (m, 1H), 6.77-6.60 (m, 1H), 6.66-6.60 (m, 2H), 4.51 (hept, J=6.1 Hz, 1H), 3.27 (t, J=6.6 Hz, 2H), 3.10 (t, J=7.0 Hz, 2H), 2.06 (quint, J=6:7 Hz, 2H), 1.34 (d, J=6.1 Hz, 6H).

Reference： [1]Patent: US2005/49239,2005,A1 .Location in patent: Page/Page column 13-14
[2]Bioorganic and medicinal chemistry,2004,vol. 12,p. 4511 - 4532

12
[ 1136-45-4 ]
[ 6276-54-6 ]
[ 334929-93-0 ]

Reference： [1]Patent: US6365591,2002,B1 .Location in patent: Example 2

13
[ 6276-54-6 ]
[ 126147-70-4 ]
[ 192725-50-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogenchloride; sodium hydroxide In tetrahydrofuran; ethanol; ethyl acetate	35.B B. B. 2S-(1-Tetrahydro-pyrimid-2-onyl)-3-methyl butanoic acid A mixture of N-phenoxycarbonyl-L-valine (25 g, 0.106 mol) and 3-chloropropylamine hydrochloride (15.2 g, 0.116 mol) in THF (250 mL) was cooled to 2° C. Sodium hydroxide (12.7 g, 0.318 mol) was added to the stirring suspension. After about 35 minutes, a slow exotherm to 10° C. occurred. The reaction was stirred at less than 10° C. for 2 hours. A solution of potassium t-butoxide (29.6 g, 0.265 mol) in 125 mL of THF was added over 10 minutes, followed by a 20 mL THF rinse. The temperature of the reaction mixture was allowed to rise to 20° C. during the addition. The reaction mixture was stirred at room temperature for 19 hours. The reaction mixture was quenched with 200 mL of distilled water and then acidified to pH 9 using 26.2 g of concentrated hydrochloric acid, keeping the temperature below 30° C. The aqueous layer was separated and washed with another 125 mL of THF. Ethanol 3A (75 mL) was added to the separated aqueous layer and the mixture was acidified to pH<3 with 12.3 g of concentrated hydrochloric acid, keeping the temperature below 25° C. The acidified mixture was extracted twice with ethyl acetate (250 mL and 150 mL). The combined organic layers were evaporated to dryness on a rotary evaporator at a temperature below 50° C. The residual solids were flushed with 250 mL of ethyl acetate. The residual solid was dissolved in 150 mL of ethanol 3A at reflux temperature and filtered through a 5 g Darco-G60 bed over filteraid, followed by a 50 mL hot ethanol rinse. The filtrate was evaporated to dryness on a rotary evaporator at a temperature below 50° C. Ethyl acetate (75 mL) was added to the residue and refluxed for 30 minutes. The suspension was cooled to below 10° C. for 2 hours. The solid was collected by filtration and washed with 20 mL of cold ethyl acetate (5-8° C.). After drying at 40° C. for 72 hours the desired product was obtained as a white solid (15.6 g, 74%).
74%	Stage #1: 3-chloropropylamine hydrochloride; (2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid With sodium hydroxide In tetrahydrofuran at 2℃; for 0.583333h; Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 19h;

Reference： [1]Current Patent Assignee: ABBVIE INC - US5914332, 1999, A
[2]Current Patent Assignee: ABBVIE INC - EP1170289, 2002, A2 Location in patent: Page 62-63

14
[ 1486-51-7 ]
[ 6276-54-6 ]
[ 530-62-1 ]
[ 222422-41-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium carbonate In water; N,N-dimethyl-formamide	87 4-Benzyloxy-N-(3-chloro-propyl)-benzamide EXAMPLE 87 4-Benzyloxy-N-(3-chloro-propyl)-benzamide A mixture of 4-benzyloxy benzoic acid (5.0 g, 21.9 mmol), 1,1,-carbonyl-diimidazole (3.6 g, 1.05 eq.) and DMF (50 ml) was stirred at 50° C. for 1 h. After cooling to r.t., 3-chloropropylamine hydrochloride (3.4 g, 26.1 mmol) and sodium carbonate (3.5 g, 32.0 mmol) were added and stirring continued for 45 min. After the addition of water, the mixture was extracted with ether. The organic layer was dried (Na2 SO4), filtered and evaporated to give 4-benzyloxy-N-(3-chloro-propyl)-benzamide (5.44 g, 85%) as a white solid. MS: me/e=304 (M+H)+.

Reference： [1]Current Patent Assignee: EVOTEC AG - US5889026, 1999, A

15
[ 73279-04-6 ]
[ 14753-26-5 ]
[ 6276-54-6 ]
[ 73278-98-5 ]

Yield	Reaction Conditions	Operation in experiment
86.0%	With sodium chloride; In sodium hydroxide; dimethyl sulfoxide; benzene;	3-Chloropropylamine hydrochloride (VI) (0.2 mol, 39 g) was dissolved into 3N sodium hydroxide solution (containing 10percent sodium chloride) and extracted with 300 ml of benzene. The benzene layer was dried over anhydrous magnesium sulfate. Separately, 3-piperidinomethylphenol (V) (0.2 mol, 38.2 g), sodium hydroxide (0.25 mol, 10 g), 100 ml of dimethylsulfoxide, and 70 ml of benzene were charged to a flask equipped with a water quantitative measurement tube, and heated at 130° C. for 3 hours while stirring to remove water produced by the tube, followed by continued stirring for 2 hours at 140°-150° C. To the resulting reaction mixture was dropwise added said benzene solution of 3-chloropropylamine at 150° C. while stirring over 4 hours. The reaction mixture was allowed to stand still to cool to room temperature to separate deposited sodium chloride by filtration. The filtrate was concentrated under reduced pressure and vacuum distilled to obtain 42.7 g of N-[3-(3-aminopropoxy)benzyl] piperidine (VII) (yield: 86.0percent). m.p. 148°-151° C./0.25 mmHg.

Reference： [1]Patent: US5317026,1994,A

16
[ 34619-03-9 ]
[ 6276-54-6 ]
[ 497-19-8 ]
[ 116861-31-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; water;	(a) N-[(tert-butoxy)carbonyl]-3-chloro-propylamine The compound of the title, employed as the starting material in example 1, is prepared by slowly adding a solution of 3-chloro-propylamine hydrochloride (12.98 g, 0.1 mol) in dioxane/water (100 ml 2/1 v/v) to a vigorously stirred mixture of di-(tert-butyl)carbonate (24 g, 0.11 mol), 1N Na2 CO3 (100 ml) and dioxane/water (200 ml, 2/1 v/v) cooled to 0 C. When the addition is over, the reaction mixture is stirred at room temperature for an additional hour, dioxane is removed under vacuum and the aqueous phase is extracted a few times with ethyl acetate. From the organic solution an oily product (19.2 g) is recovered, whose structure is confirmed by NMR spectroscopy. This compound can be used as such for the preparation of example 1.

Reference： [1]Patent: US4914226,1990,A

17
[ 589-93-5 ]
[ 6276-54-6 ]
[ 88596-89-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; sodium amide In ammonia; water	1 EXAMPLE 1 EXAMPLE 1 2,5-Dimethylpyridine (321 g) is added to a solution of sodamide (351 g) in liquid ammonia (3 1) and the mixture is stirred for 1 hour. 1-Amino-3-chloro- propane hydrochloride (429 g) is added to the stirred solution over approximately 8 minutes with stirring. After this addition, any liquid ammonia lost through evaporation is replaced. The reaction is quenched after 2 hours by the addition, with stirring, of ammonium chloride (120 g) to the reaction mixture. The ammonia is allowed to evaporate and after allowing the residue to stand (ca 16 hr), water (2 1), is added and the aqueous phase so obtained is extracted with dichloromethane and dried (Na2 SO4). The dichloromethane is evaporated and the residue is distilled in vacuo giving 4-(5-methyl-2-pyridyl)butylamine.

Reference： [1]Current Patent Assignee: FRENCH LAB; GLAXOSMITHKLINE PLC - US4526974, 1985, A

18
[ 207683-21-4 ]
[ 6276-54-6 ]
[ 138232-34-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide In water hydrochloride salt of 3-chloropropylamine is dissolved in water and added to a soln. of NaOH in water, the soln. obtained is added to a soln. of Na2PtCl4*4H2O in water (1:2 platinum-ligand ratio) and stirred for 40 min; the yellow ppt. is filtered off and washed with water, ethanol and ether; elem. anal.;

Reference： [1]Ukraintsev, V. B.; Zaitseva, T. M.; Kukushkin, Yu. N. [Journal of general chemistry of the USSR, 1991, vol. 61, p. 1174 - 1178][J.Gen.Chem.USSR (Engl.Transl.), 1991, vol. 61, p. 1293 - 1298]

19
[ 14753-26-5 ]
[ 6276-54-6 ]
[ 126147-70-4 ]
[ 192725-50-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-chloropropylamine hydrochloride; (2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid With sodium hydroxide In tetrahydrofuran at 1 - 5℃; for 2h; Stage #2: 3-chloropropan-1-amine for 1h; Stage #3: With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 12 - 16h;

Reference： [1]Current Patent Assignee: ABBVIE INC - EP1170289, 2002, A2 Location in patent: Page 63

20
[ 34619-03-9 ]
[ 6276-54-6 ]
[ 116861-31-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In chloroform; at 20℃;	[0086] Under stirring, a solution of di-tert-butyl di-carbonate (23.79 g, 110 mmol) in chloroform (50 mL) is slowly addedinto a solution of 3-chloropropylamine hydrochloride (11.0 g, 110 mmol) and triethylamine (18.42 mL, 130 mmol) inchloroform (50 mL). After stirring overnight at room temperature, a brown oil is obtained as a crude product. Thencompound (8-2) (22 g, 95%) as a colorless solid is produced by Kugelrohr distillation at a temperatures of less than 48 C.

Reference： [1]Advanced Materials,2012,vol. 24,p. 6193 - 6198
[2]Patent: EP2615092,2013,A1 .Location in patent: Paragraph 0085; 0086

21
[ 6276-54-6 ]
[ 126147-70-4 ]
C₉H₁₇ClN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In tetrahydrofuran at 2 - 10℃; for 2h; Inert atmosphere;

Reference： [1]Stoner, Eric J.; Cooper, Arthur J.; Dickman, Daniel A.; Kolaczkowski, Lawrence; Lallaman, John E.; Liu, Jih-Hua; Oliver-Shaffer, Patricia A.; Patel, Ketan M.; Paterson Jr., Joseph B.; Plata, Daniel J.; Riley, David A.; Sham, Hing L.; Stengel, Peter J.; Tien, Jien-Heh J. [Organic Process Research and Development, 2000, vol. 4, # 4, p. 264 - 269]

22
[ 156-87-6 ]
[ 6276-54-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With thionyl chloride In chloroform at 0℃; Reflux;	2-12.1 Synthesis of 3-chloropropylamine hydrochloride (8A) To solution of thionyl chloride (8.68 g, 1.32 mmol) in anhydrous chloroform (30 mL) was added dropwise to 3-aminopropan-l-ol (4.49 g, 59.19 mmol) while maintaining the temperature at 0 - 10 °C. The mixture was allowed to warm to room temperature and then heated at reflux for 3 h. The mixture was cooled to room temperature and the precipitate was collected to give 3-chloropropylamine hydrochloride (8A) (7.07 g, 55.15 mmol, 93%) as a green solid. ESMS m/z 94 (M+H)+.
93%	With thionyl chloride In chloroform at 0 - 20℃; for 3h; Reflux;	12.1 Step 1: Synthesis of 3-chloropropylamine hydrochloride (8)[00261j To solution of thionyl chloride (8.68 g, 1.32 mmol) in anhydrous chloroform (30 mL) was added dropwise to 3-aminopropan-1-ol (4.49 g, 59.19 mmol) while maintaining the temperature at 0 - 10 °C. The mixture was allowed to warm to room temperature and then heated at reflux for 3 h. The mixture was cooled to room temperature and the precipitate was collected to give 3-chloropropylamine hydrochloride (8) (7.07 g, 55.15 mmol, 93%) as a green solid. ESMS mlz 94 (M+H).
	With thionyl chloride In chloroform at 0 - 20℃;

Reference： [1]Current Patent Assignee: SOVA PHARMACEUTICALS - WO2014/18571, 2014, A2 Location in patent: Paragraph 00463
[2]Current Patent Assignee: SOVA PHARMACEUTICALS - WO2014/18570, 2014, A1 Location in patent: Paragraph 00261
[3]Uchiyama, Seiichi; Tsuji, Toshikazu; Kawamoto, Kyoko; Okano, Kentaro; Fukatsu, Eiko; Noro, Takahiro; Ikado, Kumiko; Yamada, Sayuri; Shibata, Yuka; Hayashi, Teruyuki; Inada, Noriko; Kato, Masaru; Koizumi, Hideki; Tokuyama, Hidetoshi [Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5413 - 5417][Angew. Chem., 2018, vol. 130, p. 5511 - 5515,5]

23
[ 85-44-9 ]
[ 6276-54-6 ]
[ 42251-84-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	at 160℃; for 0.25h;
74%	at 160℃; for 0.25h;

Reference： [1]Abdel-Fattah, Mohamed A. O.; Lehmann, Jochen; Abadi, Ashraf H. [Chemistry and biodiversity, 2013, vol. 10, # 12, p. 2247 - 2266]
[2]Ding, Feiqing; Guy, Adam T.; Greimel, Peter; Hirabayashi, Yoshio; Kamiguchi, Hiroyuki; Ito, Yukishige [Chemical Communications, 2018, vol. 54, # 61, p. 8470 - 8473]

24
[ 64709-55-3 ]
[ 6276-54-6 ]
N-(3-chloropropyl)-2-(pyren-1-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 7h; Inert atmosphere;	3.2.3. N-(3-Chloropropyl)-2-(pyren-1-yl)acetamide (6) 3-Chloropropylamine hydrochloride (12 mg, 0.093 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC, 17 mg, 0.089 mmol), 4,4-dimethylaminopyridine (DMAP, 1 mg 0.008 mmol) and Et3N (50 μL, 0.359 mmol) were added to a solution of 1-pyreneacetic acid (20 mg, 0.077 mmol) in anhydrous CH2Cl2 (1 mL) under an argon atmosphere. The reaction mixture was stirred at room temperature for 7 h, quenched with aqueous saturated NH4Cl solution, and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (CH2Cl2) to give 6 as a pale yellow solid (13 mg, 50%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 8.20 (2H, d, J = 7.6 Hz), 8.15 (3H, d, J = 7.9 Hz), 8.08 (1H, d, J = 9.2 Hz), 8.04 (1H, d, J = 9.2 Hz), 8.02 (1H, t, J = 7.9 Hz), 7.88 (1H, d, J = 7.9 Hz), 4.28 (2H, s), 3.31 (2H, t, J = 6.4 Hz), 3.25 (2H, q, J = 6.4 Hz), 1.78 (2H, quin, J = 6.4 Hz). 13C-NMR (125 MHz, CDCl3) δ (ppm) 171.23, 131.28, 131.16, 130.76, 129.53, 128.50, 128.16, 127.69, 127.27, 126.28, 125.60, 125.48, 125.20, 125.12, 124.62, 122.76, 42.22, 42.08, 37.28, 31.86. IR (cm-1): 3293, 1646, 1544. HR ESI-MS (m/z): calcd. for [C21H19ClNO]+, 336.1150 ([M+H]+); found 336.1161.

Reference： [1]Fuchi, Yasufumi; Obayashi, Hideto; Sasaki, Shigeki [Molecules, 2015, vol. 20, # 1, p. 1078 - 1087]

25
[ 55-22-1 ]
[ 6276-54-6 ]
N-(3-chloropropyl)isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: pyridine-4-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetonitrile at 0℃; for 1h; Stage #2: 3-chloropropylamine hydrochloride With triethylamine In acetonitrile at 20℃; for 24h;	4.1.2. Synthesis of the chloroalkylisonicotinamides (2a and 2b) General procedure: N,N'-Dicyclohexylcarbodiimide (DCC, 9.28 g, 0.045 mol) and hydroxybenzotriazole (HOBt, 6.08 g, 0.045 mol) were added to a mixture of isonicotinic acid (1) (5.00 g, 0.041 mol) in acetonitrile (50 mL) and the reaction was stirred for 1 h at 0 °C. Then, triethylamine (TEA, 4.55 g, 0.045 mol) and the appropriate 2-chloroethanamine hydrochloride (4.75 g, 0.041 mol) or 3-chloropropan-1-amine hydrochloride (5.33 g, 0.041 mol) was added to the reaction mixture and the resulting solution was stirred for 24 h at room temperature. The mixture was then cooled to 0 °C, in order to precipitate N,N'-dicyclohexylurea (DCU), and filtered. The filtrate was evaporated and after dissolution in DCM, the residue was washed with NaHCO3, water and brine. The combined organic layers were dried on anhydrous Na2SO4 and concentrated in vacuo. The crude chloroalkylisonicotinamides were purified by column chromatography (DCM/methanol 9:1 (v/v)), yielding N-(2-chloroethyl)isonicotinamide (2a, 6.71 g, 89%), Mp: 97-98 °C. 1H NMR (400 MHz, CDCl3) δ: 3.60 (q, 2H, -NH-CH2, J = 5.4); 3.85 (t, 2H, -CH2-Cl, J = 5.4); 6.99 (bs, 1H, NH); 7.61 (d, 2H, J = 5.8); 8.74 (d, 2H, J = 5.8). 13C NMR (400 MHz, CDCl3) δ: 36.54; 56.36; 121.12; 142.65; 150.84; 165.54. and N-(3-chloropropyl)isonicotinamide (2b, 6.84 g, 84%). Mp 116-118 °C. 1H NMR (400 MHz, CDCl3) δ: 1.86 (m, 2H, -CH2-CH2-CH2, J = 5.4); 3.60 (q, 2H, -NH-CH2, J = 5.4); 3.86 (t, 2H, -CH2-Cl, J = 5.4); 7.61 (d, 2H, J = 5.8); 8.35 (bs, 1H, NH); 8.69 (d, 2H, J = 5.8). 13C NMR (400 MHz, CDCl3) δ: 24.41; 41.18; 58.39; 121.61; 142.37; 150.93; 165.63.

Reference： [1]Fiorino, Ferdinando; Ciano, Antonio; Magli, Elisa; Severino, Beatrice; Corvino, Angela; Perissutti, Elisa; Frecentese, Francesco; Di Vaio, Paola; Izzo, Angelo A.; Capasso, Raffaele; Massarelli, Paola; Nencini, Cristina; Rossi, Ilaria; Kedzierska, Ewa; Orzelska-Gorka, Jolanta; Bielenica, Anna; Santagada, Vincenzo; Caliendo, Giuseppe [European Journal of Medicinal Chemistry, 2016, vol. 110, p. 133 - 150]

26
[ 73279-04-6 ]
[ 6276-54-6 ]
C₁₅H₂₄N₂O*(x)ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Take the above white solid 1500g, set microwave reactor,Adding 70percent sodium hydride 540g and anhydrous dimethylformamide 3000g,Select microwave frequency 1500MHz, the reaction 1 hour, adding sodium hydroxide 500g, potassium hydroxide 400g,Then 3-chloro propylamine hydrochloride was added1330g and anhydrous dimethylformamide 4000g, the choice of microwave frequency 2500MHz, the reaction 2 hours, filtered, the filtrate was distilled off dimethylformamide, add water 10000g, pH adjusted to 5 with acetic acid, extracted with dichloromethane 6000g, the aqueous phase Then adjust the pH to 9 with 25percent aqueous ammonia, extract with 9000 g of dichloromethane, combine the organic phases, distill and recover the dichloromethane, vacuum distillate and collect the distillate of 160-170 ° C to obtain a colorless liquid;

Reference： [1]Patent: CN106883197,2017,A .Location in patent: Paragraph 0009

27
[ 6276-54-6 ]
[ 18171-19-2 ]
C₉H₂₂ClNO₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 3-chloropropylamine hydrochloride With ammonium hydroxide for 2.5h; Cooling with ice; Stage #2: 3-chloropropylmethyldimethoxysilane In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;	3.1-3.2 (1)[HCl]·NH2(CH2)3Cl Dehydrochloric acidThe preparation concentration is 20% ammonia solution,Add [HCl]·NH2(CH2)3Cl, stir for 2.5h under ice-water bath; add ether for extraction 4 times, combine the organic layers; wash the organic layer with saturated aqueous sodium chloride solution 3 times, add anhydrous magnesium sulfate, stir and dry overnight , Filtered, the filtrate was rotary evaporated to remove the organic solvent, dried under vacuum at 20°C to constant weight to obtain NH2(CH2)3Cl. (2) Weigh 18g γ-chloropropylmethyldimethoxysilane ((CH3O)2CH3Si(CH2)3Cl), 20gNH2(CH2)3Cl and 110g dimethyl sulfoxide DCSO, and add them to the three-mouth round bottom under nitrogen protection In the flask, stir, slowly increase the temperature, and react at 120°C for 12 hours. After the reaction, let stand to cool and filter. The filtrate was distilled under reduced pressure at 80°C to remove the remaining reactants and solvent, and dried under vacuum at 35°C to a constant weight to obtain a multifunctional silane coupling agent with the molecular formula (CH3O)2CH3Si(CH2) 3NH(CH2)3Cl, the yield is about 99%.

Reference： [1]Current Patent Assignee: CRRC GROUP CORPORATION - CN111116627, 2020, A Location in patent: Paragraph 0043-0046

28
[ 5089-70-3 ]
[ 6276-54-6 ]
C₁₂H₂₈ClNO₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 3-chloropropylamine hydrochloride With potassium hydroxide for 1h; Cooling with ice; Stage #2: (3-chloropropyl)triethoxysilane In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;	1.1-1.2 (1) [HCl]·NH2(CH2)3Cl Dehydrochloric acid: Prepare a KOH solution with a concentration of 10%,Add [HCl]·NH2(CH2)3Cl, stir under ice-water bath for 1h;Add ethyl acetate to extract 3 times, combine the organic layers;The organic layer was washed 4 times with a saturated sodium chloride aqueous solution, added with anhydrous magnesium sulfate, stirred and dried all day and night, filtered, the filtrate was rotary evaporated to remove the organic solvent, and dried under vacuum at 30°C to constant weight.Obtain NH2(CH2)3Cl. (2) Weigh 24g of γ-chloropropyltriethoxysilane ((C2H5O)3Si(CH2)3Cl), 10g of NH2(CH2)3Cl and 95g of dimethylformamide, and add them to a three-necked round bottom flask under nitrogen protection. Stir, slowly increase the temperature, and react at 110 for 24h; after the reaction, let stand to cool, filter, the filtrate will be distilled under reduced pressure at 70 to remove the remaining reactants and solvents, and dried under vacuum at 30 to constant weight to obtain multifunctional Silane coupling agent, the molecular formula is (C2H5O)3Si(CH2)3NH(CH2)3Cl, the yield is about 99%.

Reference： [1]Current Patent Assignee: CRRC GROUP CORPORATION - CN111116627, 2020, A Location in patent: Paragraph 0031-0034

29
[ 1271-42-7 ]
[ 6276-54-6 ]
[ 75-50-3 ]
C₁₇H₂₅FeN₂O⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.5%	Stage #1: ferrocenecarboxylic acid; 3-chloropropylamine hydrochloride With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h; Stage #2: trimethylamine In ethanol at 60℃; for 120h;	9 Example 9. Synthesis of Compound 7 230.0mg (1.00 mmol) of ferrocenecarboxylic acid,156.0 mg (1.20 mmol) of 3-chloropropylamine hydrochloride, 513.9 mg (1.20 mmol) of (1 -cyano-2-ethoxy-2-oxoeth- ylidenaminooxy)dimethylaminomorpholinocarbeniumhexafluorophosphate (COMJJ), and 323.1 mg (2.50 mmol) of DIPEA were stirred in 10 mE of DMF. After 2 hours, the reaction was diluted with 50 mE of EtOAc, then washed successively with 1 M NaOH (3x50 mE), 1 M HC1 (3x50 mE), water (1x50 mE), 5% aqueous Na25204 (lxlOO mE), then finally 5% aqueous LiC1 (lxlOO mE). The organic phase was dried over anhydrous Na2504, filtered, and evaporated to give pure 4. Yield: 300.4 mg (98.3%) of an orange-yellow powdet 1 H NMR (500 MHz, DMSO-d5) ö 7.85 (t, 1H), 4.77 (t, 2H), 4.33 (t, 2H), 4.14 (s, 5H), 3.69 (t, 2H), 3.28 (q, 2H), 1.95 (m, 2H); 13C NMR (125 MHz, DMSO-d5) ö 168.9, 76.5, 69.7, 69.1, 68.0, 43.0, 36.1, 32.4.258.9 mg of 4 produced in the previous step was stirred with25 mE of a 4.2 M solution of trimethylamine in ethanol. The solution was sealed in a heavy-walled glass tube and heated to 60° C. for 5 days. Following that, all volatiles were removed in vacuo to give 7. Yield: 288.9 mg (93.5%) of a dark brown foam. 1H NMR (500 MHz, CDC13) ö 7.93 (t, 1H), 4.77 (t, 2H), 4.35 (t, 2H), 4.17 (s, 5H), 3.24 (m, 4H),3.06 (s, 9H), 1.91 (m, 2H); 13C NMR (125 MHz, CDC13) ö174.4, 73.6, 71.6, 70.0, 68.3, 64.3, 52.9 (3 separate peaks),36.2, 23.0.

Reference： [1]Current Patent Assignee: HARVARD UNIVERSITY - US2020/373599, 2020, A1 Location in patent: Paragraph 0100

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P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6276-54-6 ] {[proInfo.proName]}

Quality Control of [ 6276-54-6 ]

Related Doc. of [ 6276-54-6 ]

Product Details of [ 6276-54-6 ]

Calculated chemistry of [ 6276-54-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6276-54-6 ]

Application In Synthesis of [ 6276-54-6 ]

[ 6276-54-6 ] Synthesis Path-Upstream 1~3

[ 6276-54-6 ] Synthesis Path-Downstream 1~29

Related Functional Groups of [ 6276-54-6 ]

Aliphatic Chain Hydrocarbons

Chlorides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 6276-54-6 ]