[ CAS No. 93138-61-5 ]

Name: 93138-61-5|(1-Benzylpyrrolidin-3-yl)methanamine|98%
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SKU: A525172
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Quality Control of [ 93138-61-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 93138-61-5 ]

CAS No. :	93138-61-5	MDL No. :	MFCD06411056
Formula :	C₁₂H₁₈N₂	Boiling Point :	284.3°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	190.28 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 93138-61-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P301+P310+P330-P305+P351+P338	UN#:	2810
Hazard Statements:	H300-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 93138-61-5 ]

Upstream synthesis route of [ 93138-61-5 ]
Downstream synthetic route of [ 93138-61-5 ]

[ 93138-61-5 ] Synthesis Path-Upstream 1~1

1
[ 24424-99-5 ]
[ 93138-61-5 ]
[ 155497-10-2 ]

Reference： [1] Patent: US6166015, 2000, A,
[2] Patent: US2003/236277, 2003, A1, . Location in patent: Page 27

[ 93138-61-5 ] Synthesis Path-Downstream 1~24

1
[ 108282-38-8 ]
[ 93138-61-5 ]
4-Amino-N-(1-benzyl-pyrrolidin-3-ylmethyl)-5-chloro-2-ethoxy-benzamide [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1364 - 1378

2
2-(1-benzyl-pyrrolidin-3-ylmethyl)-isoindole-1,3-dione [ No CAS ]
[ 93138-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In ethanol for 2h; Heating;
	With hydrazine hydrate In ethanol for 2h; Heating;

Reference： [1]Itoh, Katsuhiko; Kanzaki, Koji; Ikebe, Tsuguo; Kuroita, Takanobu; Tomozane, Hideo; Sonda, Shuji; Sato, Noriko; Haga, Keiichiro; Kawakita, Takeshi [European Journal of Medicinal Chemistry, 1999, vol. 34, # 4, p. 329 - 341]
[2]Itoh, Katsuhiko; Kanzaki, Koji; Ikebe, Tsuguo; Kuroita, Takanobu; Tomozane, Hideo; Sonda, Shuji; Sato, Noriko; Haga, Keiichiro; Kawakita, Takeshi [European Journal of Medicinal Chemistry, 1999, vol. 34, # 11, p. 977 - 989]

3
[ 93138-61-5 ]
C₁₅H₁₈ClNO₅ [ No CAS ]
N-[(1-benzyl-3-pyrrolidinyl)methyl]-6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzoxazine-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate at -10℃;

4
[ 7206-70-4 ]
[ 93138-61-5 ]
4-amino-N-[(1-benzyl-3-pyrrolidinyl)methyl]-5-chloro-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-amino-5-chloro-2-methoxybenzoic acid; C-(1-benzyl-pyrrolidin-3-yl)-methylamine With benzotriazol-1-ol In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;
	Stage #1: 4-amino-5-chloro-2-methoxybenzoic acid; C-(1-benzyl-pyrrolidin-3-yl)-methylamine With benzotriazol-1-ol In N,N-dimethyl-formamide for 1h; cooling; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;

5
[ 93138-61-5 ]
[ 134372-44-4 ]
N-[(1-benzyl-3-pyrrolidinyl)methyl]-6-chloro-3,4-dihydro-4-methyl-2H-1,4-benzoxazine-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid With triethylamine; isobutyl chloroformate In ethyl acetate at -10℃; Stage #2: C-(1-benzyl-pyrrolidin-3-yl)-methylamine In ethyl acetate at -10℃;

6
[ 5731-17-9 ]
[ 93138-61-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 977 - 989
[2]European Journal of Medicinal Chemistry,1999,vol. 34,p. 329 - 341

7
[ 24424-99-5 ]
[ 93138-61-5 ]
[ 155497-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; dichloromethane;	Step 3 3-(RS)-Aminomethyl-1-benzylpyrrolidine (14.7 g, 80 mmol) was dissolved in methylene chloride (400 mL) with stirring. A solution of di-tert-butyl dicarbonate (16.8 g, 80 mmol, 1.0 equiv.) in methylene chloride (50 mL) was added dropwise and the reaction mixture was stirred overnight. The reaction mixture was concentrated and the residue was dissolved in diethyl ether (400 mL) and extracted with NaHSO4 solution (1 M, 120 mL). The aqueous layer was basified to pH 12 with 1 M sodium hydroxide and extracted with ethyl acetate. The organic fractions were combined, washed with brine, dried over magnesium sulfate, and filtered. The organics were evaporated to afford 1-benzyl-3-(RS)-(N-tert-butoxycarbonylaminomethyl)pyrrolidine (22.5 g) which was used directly.
	With triethylamine; In dichloromethane; at 20.0℃; for 3.0h;	A mixture of crude amine (0.028 mol, 5.3 g), triethylamine (0.034 mol, 4.7 mL), and and ditertbutyl dicarbonate (0.034 mol, 7.4 g) in dichloromethane was stirred at ambient temperature for 3 h. The reaction was diluted with dichloromethane, and then washed with water and then sat aq NaCl. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Purification via flash chromatography over silica gel provided 4.2 g of the desired carbamate. 1H NMR (300 MHz, CDCl3): 7.327.30(m, 5H), 3.593.58(m, 2H), 3.173.02(m, 2H), 2.732.28(m, 5H), 2.041.90(m, 1H), 1.601.48(m,1H), 1.45(s,9H).

Reference： [1]Patent: US6166015,2000,A
[2]Patent: US2003/236277,2003,A1 .Location in patent: Page 27

8
[ 10603-52-8 ]
[ 93138-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 18h;	This reaction was carried out according to the procedure in M. R. Pavia et.al. reference 98. The nitrite (0.03 mol, 5.5 g) was dissolved in THF and cooled to 0 C. Lithium aluminum hydride (0.03 mol, 1.14 g) was added into the solution in one portion. After the addition was finished, the colling bath was removed and the reaction was stirred at ambient temperature for 18 h. The reaction was filtered and the filtrate was aconcentrated in vacuo to provide the crude product which was used directly in the next reaction.

Reference： [1]Patent: US2003/236277,2003,A1 .Location in patent: Page 26-27

9
aqueous potassium carbonate [ No CAS ]
[ 24424-99-5 ]
[ 93138-61-5 ]
1-benzyl-3-(tert-butoxycarbonylaminomethyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane	P.9 PREPARATION EXAMPLE 9 PREPARATION EXAMPLE 9 Methylene chloride (1000 ml) was added to (1-benzylpyrrolidin-3-ylmethyl)amine (112 g), and a solution of di-tert-butyl dicarbonate (141 g) in methylene chloride was dropwise added at 0° C. with stirring. The mixture was stirred at room temperature for 8 hr. Aqueous potassium carbonate solution was added and the mixture was extracted with chloroform. The mixture dried over magnesium sulfate, and concentrated under reduced pressure to give 171 g of 1-benzyl-3-(tert-butoxycarbonylaminomethyl)pyrrolidine. m.p. 51°~54° C.

Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - US5864039, 1999, A

10
[ 116041-19-1 ]
[ 7757-82-6 ]
[ 93138-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran	4.2 Step 2 Step 2 1-Benzyl-5-oxo-pyrrolidine-3-carboxylic acid amide (22 g, 0.1 mol) was added portionwise to a stirred solution of lithium aluminum hydride (9.5 g, 0.25 mol, 2.5 equiv.) in dry tetrahydrofuran (600 mL). After the initial effervescence had subsided, the reaction mixture was heated at reflux at room temperature for 24 h, at which time analysis of the reaction mixture by LCMS showed there was no starting material. The reaction mixture was quenched by dropwise addition of saturated sodium sulphate solution with stirring until no further effervescence was observed. The suspension was filtered through a celite plug, eluding with diethyl ether (200 mL). The solvent was remove to afford 3-(RS)-aminomethyl-1-benzylpyrrolidine as an oil (14.7 g) which was used directly without further purification.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US6166015, 2000, A

11
[ 93138-61-5 ]
[ 98-59-9 ]
1-benzyl-3-(p-toluenesulfonyl)aminomethylpyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; dichloromethane; water	R.1 3-(2-fluoroethyl)aminomethylpyrrolidine REFERENCE EXAMPLE 1 3-(2-fluoroethyl)aminomethylpyrrolidine To a solution of 1-benzyl-3-aminomethylpyrrolidine (J. Org. Chem. 26 4955, 1961; 5.0 g) in pyridine (30 ml) was added p-toluenesulfonyl chloride (5.6 g) for 5 minutes, and stirred for 2 hours at room temperature. After the reaction mixture was allowed to stand overnight and concentrated. The residue contain pyridine was removed by azeotrope with water (20 ml). A solution of the resulting residue in dichloromethane (100 ml) was washed with aqueous solution of potassium carbonate (x 2) and water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography eluding with methanol:acetonitrile:dichloromethane (0:1:3→0.5:1:3) to give 1-benzyl-3-(p-toluenesulfonyl)aminomethylpyrrolidine (5.31 g) as liquid.

Reference： [1]Current Patent Assignee: KYORIN HOLDINGS, INC. - US4791118, 1988, A

12
[ 935670-88-5 ]
[ 93138-61-5 ]
C₃₀H₃₇N₇O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₂₀H₂₅N₅O₆; C-(1-benzyl-pyrrolidin-3-yl)-methylamine With triethylamine In ethanol for 72h; Heating / reflux; Stage #2: With PS-isocyanate; PS-Trisamine scavenger reagent In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;	A.A2.e P.r.?P.aration gf. intermediate.8A mixture of intermediate 7 (0.000058 mol), l-(phenylmethyl)- 3- pyrrolidinemethanamine (0.000115 mol) and triethylamine (0.00035 mol) in EtOH (10 ml) was stirred and refluxed for 3 days and then the solvent was evaporated. The residue was dissolved in DCM/DMF (4/1) (10 ml) and then Tris-(2-aminomethyl)- amine polystyrene HL (200-400mesh),l%DVB (Novabiochem 01-64-0170) (0.100 g) and methylisocyanate polystyrene HL(200-400mesh),2%DVB (Novabiochem 01-64- 0169) (0.100 g) were added. The resulting mixture was shaken for 20 hours at room temperature and the resins were filtered off. The filtrate was evaporated and the obtained residue was used as such in the next reaction step, yielding 0.050 g of intermediate 8.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2007/48767, 2007, A1 Location in patent: Page/Page column 24

13
[ 93138-61-5 ]
[ 407-25-0 ]
[ 849632-74-2 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 0 - 20℃; for 12h;	1.a 1,1-Dimethylethyl (3RS)-3-(aminomethyl)-l-pyrrolidinecarboxylate(a) 2,2,2-Trifluoro-N- { [(3RS)- l-(phenylmethyl)-3-pyrrolidinyl] methyl} acetamideN-benzyl-3(i?5)-aminomethylpyrrolidine (160 g) was dissolved in 1.6 L DCM and cooled to 0 °C. Trifluoroacetic anhydride (320 mL) was slowly added and the reaction mixture was allowed to warm to room temperature and stirred for 12 hr. The reaction mixture was washed with water (2 x 750 mL), brine (2 x 500 mL), dried over sodium sulfate and evaporated under reduced pressure to afford 190 g of the titled compound, which was used without further purification.
190 g	In dichloromethane at 0 - 20℃; for 12h;	1.a Intermediate 1 1 ,1 -Dimethylethyl (3 ?S)-3-(aminomethyl)-1 -pyrrolidinecarboxylate (a) 2,2,2-Trifluoro-N-[(3 ?S)-1 -(phenylmethyl)-3-pyrrolidinyl]methyl}acetamideN-benzyl-3(RS)-aminomethylpyrrolidine (160 g) was dissolved in 1.6 L DCM and cooled to 0 °C. Trifluoroacetic anhydride (320 ml.) was slowly added and the reaction mixture was allowed to warm to room temperature and stirred for 12 hr. The reaction mixture was washed with water (2 x 750 mL), brine (2 x 500 mL), dried over sodium sulfate and evaporated under reduced pressure to afford 190 g of the titled compound, which was used without further purification.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/56635, 2011, A1 Location in patent: Page/Page column 47
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2013/28445, 2013, A1 Location in patent: Page/Page column 49; 50

14
[ 93138-61-5 ]
[ 270912-72-6 ]

Reference： [1]Patent: WO2011/56635,2011,A1
[2]Patent: WO2013/28445,2013,A1

15
[ 93138-61-5 ]
[ 1301188-94-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloromethane / 12 h / 0 - 20 °C 2: hydrogen / palladium(II) hydroxide; palladium 10% on activated carbon / acetic acid; methanol / 48 h / 20 °C 3: triethylamine / methanol / 24 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: dichloromethane / 12 h / 0 - 20 °C 2.1: palladium 10% on activated carbon; hydrogen; palladium(II) hydroxide; acetic acid / methanol / 48 h / 20 °C 3.1: triethylamine / methanol / 0.5 h / 0 °C 3.2: 24 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/56635, 2011, A1
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2013/28445, 2013, A1

16
[ 93138-61-5 ]
[ 1301189-87-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: dichloromethane / 12 h / 0 - 20 °C 2: hydrogen / palladium(II) hydroxide; palladium 10% on activated carbon / acetic acid; methanol / 48 h / 20 °C 3: triethylamine / methanol / 24 h / 0 - 20 °C 4: sodium hydroxide; water / methanol / 3 h / 20 °C 5: dimethyl sulfoxide / 17 h / 98 °C / Inert atmosphere