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Chemical Structure| 51857-17-1
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Product Details of [ 51857-17-1 ]

CAS No. :51857-17-1 MDL No. :MFCD00671489
Formula : C11H24N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RVZPDKXEHIRFPM-UHFFFAOYSA-N
M.W : 216.32 Pubchem ID :2733170
Synonyms :

Calculated chemistry of [ 51857-17-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 9
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 62.21
TPSA : 64.35 Ų

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) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.67
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 2.03
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 1.39
Consensus Log Po/w : 1.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.48
Solubility : 7.13 mg/ml ; 0.033 mol/l
Class : Very soluble
Log S (Ali) : -2.38
Solubility : 0.91 mg/ml ; 0.00421 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.91
Solubility : 0.267 mg/ml ; 0.00124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.23

Safety of [ 51857-17-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51857-17-1 ]

* 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 [ 51857-17-1 ]
  • Downstream synthetic route of [ 51857-17-1 ]

[ 51857-17-1 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 124-09-4 ]
  • [ 24424-99-5 ]
  • [ 51857-17-1 ]
YieldReaction ConditionsOperation in experiment
84% at 0 - 20℃; for 18 h; General procedure: To a cooled (0°C) suspension of 1,6-diaminohexane (20.0 g, 172 mmol) in 50 mL DCM was added a solution of Boc2O(3.75 g, 17.2 mmol) in 24 mL DCM. After the addition the ice bath was removed and the mixture was stirred at rt for 18 h. Afterwards the precipitates were filtered and the filtrate was washed with sat. aqueous NaHCO3(3 x 50 mL). The organic layer was washed with H2O(2 x 50 mL) and brine (50 mL), dried over Na2SO4,filtered and concentrated to get 3.1 g (84 percent) of oil. 1HNMR (300 MHz, CDCl3) δ 4.56 (s,1H), 3.09 (dd, J = 12.6, 6.3 Hz, 2H), 2.83 – 2.58 (t, 2H), 1.66 – 1.17(m, 17H).
81.2% With triethylamine In dichloromethane; water REFERENCE EXAMPLE 13
Preparation of N-(t-butoxycarbonyl)hexamethylenediamine
A solution of 27.9 g (240 mmole) of hexamethylenediamine and 24.3 g (240 mmole) of triethylamine dissolved in 400 ml of methylene chloride was cooled with an ice-salt bath and to the solution was added dropwise a solution of 17.46 g (80 mmole) of di-t-butyl dicarbonate dissolved in 100 ml of methylene chloride over about 1.5 hours.
After allowed to stand at room temperature overnight, the mixture was further stirred at room temperature for one day.
The reaction mixture was washed successively with 300 ml of water once and 100 ml of the same twice.
Subsequently, the methylene chloride layer was dried over anhydrous sodium sulfate, and condensed under reduced pressure.
When the resulting red-brownish oily product was allowed to stand at room temperature, it gradually crystallized.
This crystal was dispensed by silica gel column chromatography using a developing solvent of methanol: 28percent aqueous ammonia=19:1 to give 14.05 g (Yield: 81.2percent) of a red-brownish liquid.
80% at 0 - 20℃; for 24 h; Solution of Boc2O (0.5 M; 1.83 g; 8.6 mmol) in CHCl3 (17 mL) was added dropwise to a stirred icecooled0.25 M solution of 1,6-hexanediamine 8 (5.00 g; 43.0 mmol) in CHCl3 (172 mL), for 6 h. Stirring wascontinued at room temperature for the next 18 h. Suspension was filtered over a sintered funnel and the solvent wasevaporated under vacuum. The residual mixture was redissolved in EtOAc (50 mL), washed with a saturated aqueousNaCl solution (4×15 mL), and dried over anh. Na2SO4. Solvent was removed under vacuum, yielding 9 as colorlessoil (1.48 g, 80percent). Further purification was not necessary. (If it is necessary, product may be purified by DCFC onsilica-gel, with solvent mixtures EtOAc/MeOH/NH3 (80:20:3→80:20:10) as eluents). IR(ATR): 3363, 2931, 1700,1176, 871 cm-1; 1H NMR (200 MHz, CDCl3): δ=4.97 (s, 1H, NH-Boc), 3.10 (q, J=6.2 Hz, 2H, H2C-NHBoc), 2.68 (t,J=6.2 Hz, 2H, H2C-NH2), 1.44 (s, 9H, H3CBoc), 1.52 (s, 2H, NH2), 1.51-1.25 (m, 8H, H2C2-5) ppm; 13C NMR (50MHz, CDCl3): δ=155.9 (COBoc), 78.5 (CBoc), 41.8 (CH2-NH2), 40.2 (CH2-NHBoc), 33.3, 29.8 (2CH2), 28.1 (CH3Boc),26.3, 26.2 (2CH2) ppm; ESI-TOF-MS: m/z: Calculated for C11H25N2O2: 217.1910 [M+H]+; found 217.1912.
79% at 20℃; EXAMPLE 1
Synthesis of tert-Butyl-6-aminohexylcarbamate.
To a suspension of 1,6-diaminohexane (15.97 g, 137.46 mmol) in 125 ml of dichloromethane, was slowly added di-tert-butyl dicarbonate solution (10.00 g, 45.82 mmol in 75 ml of dichloromethane).A slightly cloudy suspension was formed after the addition was completed.The resulting mixture was stirred at room temperature for overnight.The mixture was filtered over a layer of Celite, and the solid was thoroughly washed with dichloromethane.The filtrate was concentrated under reduced pressure to give the yellowish oil.The crude oil product was dissolved in 200 ml of ethyl acetate, and washed with water (25 ml), brine (30 ml).The organic phase was dried over sodium sulfate, then filtered and evaporated to dryness to afford the title compound as a light yellowish semi-solid (7.81 g). Yield: 79percent; 1H-NMR (CDCl3) δ ppm: 4.50-4.65 (br s, 1H); 3.1 (s, 2 H), 2.69 (s, 2 H), 1.44-1.26 (m, 17 H); MS (m/z) 217(M++1); IR (Nujol): 3370 (NH2), 1687 (C=O).
79% at 20℃; To a suspension of 1,6-diaminohexane (15.97g, 137.46 mmol) in 125 ml of dichloromethane, was slowly added di-tert-butyl dicarbonate solution (10.00 g, 45.82 mmol in 75 ml of dichloromethane). A slightly cloudy suspension was formed after the addition was completed. The resulting mixture was stirred at room temperature for overnight. The mixture was filtered over a layer of Celite, and the solid was thoroughly washed with dichloromethane. The filtrate was concentrated under reduced pressure to give the yellowish oil. The crude oil product was dissolved in 200 ml of ethyl acetate, and washed with water (25 ml), brine (30 ml). The organic phase was dried over sodium sulfate, then filtered and evaporated to dryness to afford the title compound as a light yellowish semi-solid (7.81g). Yield: 79 percent; <1>H-NMR (CDCl3) delta ppm: 4.50-4.65 (br s, 1H); 3.1 (s, 2 H), 2.69 (s, 2 H), 1.44-1.26 (m, 17 H); MS (m/z) 217(M<+>+1); IR (Nujol): 3370 (NH2), 1687 (C=O).
76% With triethylamine In dichloromethane at 20℃; for 18 h; 1,6-Diaminohexane (10 g, 0.086 mol) and Et3N (13.05 g, 18.13 mL, 0.129 mol) were suspended in CH2Cl2 (300 mL). A solution of di-tert-butyl dicarbonate (9.39 g, 0.043 mol) in CH2Cl2 (100 mL) was added dropwise over 90 min at rt and stirring continued for 18 h. The reaction mixture was added to a seperatory funnel and washed with water (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was chromatographed [CH2Cl2/MeOH-NH3 (7 N), 70:1-20:1] to give 7.1 g (76percent) of 3. 1H NMR (CDCl3) δ 4.50 (br s, 1H), 3.11 (br s, 2H), 2.68 (t, J = 6.6 Hz, 2H), 1.44 (s, 13H), 1.33 (s, 4H); MS (ESI): m/z 217.2 [M+H]+.
70.5% at 20℃; for 6 h; Cooling with ice As shown in Figure 2, 15.97 g (137.46 mmol) of hexamethylene diamine was dispersed in 300 mL of methanol in a 500 mL round bottom flask.After stirring for 0.5 h in an ice bath, a solution of hexamethylene diamine in methanol was obtained.Then di-tert-butyl dicarbonate (BOC) 2O 10g (45.82 mmol) was dissolved in 100 mL of methanol.Add a constant pressure dropping funnel (150mL) and add dropwise a solution of hexamethylene diamine in methanol on an ice bath.It is advisable to add it for less than 30 minutes and then react for 6 hours at room temperature.After the reaction was completed, the solvent was evaporated under reduced pressure to obtain a white solid.The solid was dispersed in 300 mL of deionized water and extracted with ethyl acetate (60 mL, 5 extractions).The ethyl acetate layer was collected, and the volume of ethyl acetate was concentrated under reduced pressure to 100 mL. Then, an aqueous solution of hydrochloric acid of pH=4 was added to the concentrated ethyl acetate solution, and the system was adjusted to pH=5 and stirred at room temperature for 20 min.Then, the hydrochloride BOC-C6-NH3+Cl- was extracted with deionized water (20 mL, 5 times) and the aqueous layer was collected.Take 1M sodium hydroxide solution to adjust the pH of the aqueous layer to about 9 and store at -20°C for 3 hours, and then freeze-dry to obtain a white solid, product 2: tert-butyl-(6-aminohexyl)-carbamate. yield is 70.5percent.
66.9%
Stage #1: With hydrogenchloride In methanol; water for 0.333333 h;
Stage #2: for 0.5 h;
Stage #3: at 20℃; for 1 h;
Concentrated hydrochloric acid (1.91 mL, 0.0229mol) was added to 30 mL methanol (MeOH) and cooled to 0C. 1,6-diaminohexane (2.66 g,0.0229 mol) was added to the acidified methanol and stirred for 20 min. Deionized water (10 mL) was added stirred for 30 minutes. Di-tert-butyl dicarbonate (7.90 mL, 0.0344 mol) inMeOH (40 mL) was added dropwise over 10 minutes to the diamine solution. The reaction wasallowed to come to room temperature over 1 h with stirring. The solvent was removed in vacuoand the resulting solid washed with diethyl ether (3x 30 mL). Sodium hydroxide (1 M) wasadded and the product was extracted 2x with CH2Cl2. The organic layers were combined, washedwith brine, dried over CaCl2, and concentrated in vacuo to yield a white solid (3.31 g, 66.9percentyield). ESI [M+H]+1 expected 217.33 Da, observed 217.18 Da
55.3% at -10℃; for 26 h; A solution of DI-TERT-BUTYL dicarbonate (3 g, 0.014 moles) in DCM (12 ML) was added over a period of 2 hr. to a solution of 1, 6-DIAMINOHEXANE (12 g, 0.11 moles) in DCM (36 mL) that was cooled TO-10 °C. The mixture was stirred for 24 HRS. before the solvent was removed under vacuum. Water (60 mL) was added to the residue and the insoluble bis-substituted product was collected by filtration. The filtrate was extracted using DCM (3 x 60 mL) and then dried over NA2S04 before the solvent was evaporated. The residue was dissolved in chloroform and any UNDISSOLVED product was filtered. The filtrate was then evaporated under vacuum to yield the product as a slightly yellow oil. Yield (4.12 g, 55. 3percent). H NMR (CDCl3) : 9.8 (bs, 1H, NH), 4.45 (bs, 2H, NH2), 3 (b, 4H), 2.6 (b, 4H), 2.15 (b, 4H), 1.25 (s, 9H).
54% at 20℃; N-(tert-butyloxycarbonyl)hexamethylenediamine (N-Boc-hexamethylenediamine) was obtained by treatment of hexamethylenediamine (9.30 g, 80 mmol) with di-tert-butyl dicarbonate (9.28 mL, 40 mmol) in anhydrous methanol (80 mL) at room temperature.The mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water (80 mL) and saturated with sodium carbonate. The aqueous layer was exacted with ethyl acetate (40 mL) by three times. The combined organic layers were dried by magnesium sulfate anhydrous and evaporated to give compound 2 as a yellow oil. Yield (9.33 g), percentage yield (54percent). IR/cm-1: 3349, 2980, 2929, 1693, 1529, 1450, 1360, 1250, 1172, 864. 1H NMR (CDCl3, 400 MHz, δ/ppm): 4.71 (s, 1H, -NH-), 3.06 (t, 2H, -NHCH2-), 2.63 (t, 2H, -CH2- close to amino), 1.64 (s, 2H, -NH2), 1.00-1.50 (s, 17H, -CH3, -CH2-). ESI-MS (m/z): 216. Found: 217 [M + H]+. Analysis calcd. for C11H24N2O2, C: 61.11, H: 11.11, N: 12.96. Found: C: 61.15, H: 11.14, N: 13.03 [see SI-Figs. 4-6].
42% at 0 - 20℃; for 12 h; Di-tert-butyl dicarbonate (4.0g, 18.4mmol) was dissolved in CHCl3 and added drop-wise to a solution of hexamethylenediamine (10.6g, 91.6mmol) in CHCl3 at 0°C. The mixture was allowed to warm to room temperature. After stirring for 12h, the reaction crude was filtered and washed with CHCl3. The filtrates were collected and solvent was evaporated. The residue was re-dissolved in EtOAc and washed with water and then brine. The organic solution was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 1.68g, Yield: 42percent of tert-butyl (6-aminohexyl)carbamate (2). 1H NMR (CDCl3, 400MHz): δ 4.52 (bs, 1H), 3.10 (q, J=6.6Hz, 2H), 2.68 (t, J=7.0Hz, 2H), 1.49–1.30 (m, 17H), 1.25 (t, J=7.2Hz, 2H). 13C NMR (100MHz, CDCl3): δ 156.1, 79.1, 42.2, 40.5, 33.8, 30.2, 28.4, 26.7, 26.6.
17.9% at 20℃; for 26.5 h; Cooling with ice (BOC) 2O (1.0 g, 4.6 mmol) was dissolved in 12 mL of CH 2 Cl 2 and added dropwise to the 1,6-hexanediamine (4.1 g, 35.6 mmol) in an ice water bath over 2.5 h.Then react at room temperature for 24 h, TLC (developing solvent is dichloromethane: methanol: triethylamine =100:10:1) After determining the reaction raw material a to a certain extent,Then, the unreacted 1,6-hexanediamine is washed by adding an appropriate amount of water, and the filtrate is extracted with CH2Cl2, and the organic layer is dried with Na2SO4.The solvent was removed by a rotary evaporator, and the crude product was purified by column chromatography (eluent: methylene chloride:methanol: triethylamine = 100:10:1).Separation and purification gave a colorless liquid b (1.4 g), yield 17.9percent.

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  • 2
  • [ 129392-87-6 ]
  • [ 51857-17-1 ]
YieldReaction ConditionsOperation in experiment
97% at 20℃; for 1 h; A solution of di-t-butyldicarbonate (18.6 g, [85.] 3 mmol) in dry DCM (100 [ML)] was added dropwise to a stirred solution of 6- aminohexanol (10.0 g, 85.3 mmol) in dry DCM (100 [ML)] at 20 [°C] and stirred for 16 h. The solution was washed with dilute aqueous [NA2C03] solution (100 mL), 0.1 M HC1 (100 mL), water (100 mL), brine (50 mL), dried and the solvent evaporated. The residue was dissolved in DCM (250 mL) and Et3N (15.5 mL, 111 mmol) added. A solution of methanesulfonyl chloride (7.3 mL, 94 mmol) was added dropwise and the mixture stirred at [20 °C] for 16 h. The solution was washed with saturated aqueous [KHC03] (100 mL), water (2 x 100 mL), brine (50 mL), dried, and the solvent evaporated. The residue was dissolved in DMF (100 [ML)] and NaN3 [(5.] 55 g, [85.] 3 mmol) added. The mixture was stirred at [100 °C] for 1 h, the solvent evaporated and the residue partitioned between EtOAc (200 mL) and water (200 mL). The organic fraction was washed with water (200 mL), brine (100 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with 30percent EtOAc/pet. ether, to give the [6-T-BUTYLOXYCARBAMOYLHEXYL] azide (17.5 g, 85percent) as a colorless [OIL, 1H NMR 8] 4.53 (br s, 1 H, OCONH), 3.52 (t, J= 6.9 Hz, 2 H, [CH2N),] 3.11 (dt, [J=] 6.5, 6.4 Hz, 2 H, [CH2N),] 1.57-1. 63 (m, 2 H, [CH2),] 1.44-1. 52 (m, 11 H, CH2, C [(CH3)] 3), 1.30-1. 40 (m, 4 H, 2 x [CH2), 13C NMR 8] 156.0, 79.1, 51.3, 40.4, 29.9, 28.7, 28.4 (3), 26.4, 26.3. [A] mixture of azide (14.81 g, 61.1 mol) and Pd/C (0.5 g) in EtOAc/EtOH (200 mL) was stirred at [20 °C] under hydrogen (60 psi) for 1 h. The mixture was filtered through celite, the cake washed with EtOAc [(3 X 30] mL) and the solvent evaporated to give 4 (12.82 g, [97percent)] as a white solid, mp (EtOAc) [89-91 °C] ; 1H NMR 8 4.65 (br s, 1 H, OCONH), 3.52 (br s, 2 H, NH2), 2.69 (t, [J=] 6.9 Hz, 2 H, CH2N), 1. 88 (br s, 2 H, CH2N), 1.44-1. 50 [m, 13 H, 2 x [CHA,] C (CH3) 3], 1.29-1. 35 (m, 4 H, 2 x [CHEZ) ; 13C] NMR 8 156.0, 78.9, 41.9, 40.4, 33.4, 29.9, 28.3 (3), 26.5, 26.4.
Reference: [1] Patent: WO2004/26846, 2004, A1, . Location in patent: Page 54
  • 3
  • [ 124-09-4 ]
  • [ 6627-89-0 ]
  • [ 51857-17-1 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: at 78℃; Inert atmosphere
Stage #2: With hydrogenchloride In dichloromethane; water
Stage #3: With sodium hydroxide In dichloromethane; water
tert-Butyl phenyl carbonate (25.6OmL, 138.0 mmoles) was added to a stirred solution of 1,6- diaminohexane (15.3Og, 131.7 mmoles) in absolute EtOH (15OmL) in a 25OmL RB flask. The apparatus was fitted with a condenser and heated to 780C overnight under a blanket of nitrogen and then allowed to cool to room temperature. The solvent was stripped off the reaction mixture in vacuo (rotary evaporator) yielding a pale pink oily residue. CH2Cl2 (20OmL) was added to the residue and the resultant solution extracted with 3>;<;200mL portions of de-ionised water. For each extraction the pH of the aqueous phase was monitored and adjusted with HCl(aq, 2M) such that the pH of the aqueous layer was 3 <; pH <; 7 [only required for 1st extraction, needing ca. 60-7OmL HCl(aq, 2M)]. The aqueous phases were collected in a Erlenmeyer flask containing aqueous NaOH (aq, 10OmL, 3M). Ensuring that the pH of the collected aqueous extracts was >;14 the resulting aqueous phase was extracted with CH2Cl2 (3>;<;150mL). These organic phases were recombined, evaporated to a volume of ca. 20OmL and subjected to the above pH modulated purification protocol for a second time by first extracting with water [3χ200mL, 3 <; pH <; 7 modulation with HCl(aq, 2M), again only required for 1st extract needing ca. 45-55mL HCl(aq, 2M)], basicifying these aqueous extracts with NaOH (10OmL, 3M) and extracting with CH2Cl2 (3 x 15OmL). The CH2Cl2 extracts were combined, reduced in volume to 20OmL and then dried over anhydrous MgSO4, filtered, and stripped to dryness on a rotary evaporator for a period of 20 minutes to yield 6-(tert-butoxycarbonylamino)hexylamine as a peach oil. This peach oil was then subjected to a short path distillation using a Kugelrohr apparatus with an oven temperature of 18O0C and at a vacuum pressure of 0.160 torr, the receiver bulb was cooled by means of a dry-ice / acetone bath. Yield: 13. Ig (46percent, colourless oil). 1H NMR (CDCl3) δ 1.14 (s, 2H, -NH2), 1.26-1.37 (m, 4H, -CH2-), 1.37-1.52 (s+m, 9H+4H, f-Bu + -CH2-), 2.67 (t, 2H, >;NCH2-), 3.09 (q, 2H, -C(O)NCH2-), 4.60 (bs, IH, -C(O)NH-).
Reference: [1] Synthesis, 2002, # 15, p. 2195 - 2202
[2] Organic Syntheses, 2007, vol. 84, p. 209 - 214
[3] Patent: WO2010/116142, 2010, A2, . Location in patent: Page/Page column 69-70
[4] Chemical Communications, 2009, # 43, p. 6557 - 6559
[5] Organic and Biomolecular Chemistry, 2008, vol. 6, # 16, p. 2988 - 2994
[6] Patent: US2013/281515, 2013, A1, . Location in patent: Paragraph 0180; 0181
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Reference: [1] Synthetic Communications, 1990, vol. 20, # 16, p. 2559 - 2564
[2] Organic Letters, 2015, vol. 17, # 3, p. 422 - 425
[3] Tetrahedron Letters, 2006, vol. 47, # 46, p. 8039 - 8042
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4209 - 4214
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
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YieldReaction ConditionsOperation in experiment
49% With hydrogenchloride; sodium hydroxide In ethanol; water Preparation 8
Preparation of 6-(t-butoxycarbonylamino)hexylamine
A solution of 1,6-diaminohexane (14 g, 0.12 mol) in ethanol (500 mL) was mixed with a solution of di-t-butyl carbonate (23 g, 0.1 mol) in ethanol (500 mL) and stirred overnight.
The mixture was filtered, concentrated and the residue was shaken with a mixture of ether (200 mL) and water (50 mL).
The aqueous phase was extracted twice with ether (50 mL) and the organic phase was extracted sequentially with brine, cold 0.4N hydrochloric acid (150 mL) and water (2*100 mL).
The pH of the acidic extract was brought to 12-13 with 1N sodium hydroxide and it was extracted twice with ether (50 mL).
The organic phase was washed with brine, dried (sodium sulfate) and concentrated to yield the title compound (13.16 g, 49percent). TLC Rf 0.53 (Kieselgel 60 F254, 15:3:2 2-butanol:formic acid:water); MS(ES) m/e 217.0; 1NMR (400 MHz, CDCl3): δ4.57 (br s, 1H), 3.10-3.12 (m 2H), 2.68-2.71 (m 2H), 1.84 (br s 2H), 1.44-1.48 (br s 9H), 1.32-1.34 (br s 8H).
Reference: [1] Patent: US6403578, 2002, B1,
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Reference: [1] Patent: CN106337187, 2018, B, . Location in patent: Paragraph 0039-0040; 0043; 0059; 0075
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YieldReaction ConditionsOperation in experiment
77% With triethylamine In chloroform; acetone The t-Boc protecting group is then hydrolyzed to give the product.
To prepare the monoprotected diamine N-(t-butyoxycarbonyl)-1,6-diaminohexane, first 9.4 g (81.2 mmol) of 1,6-diaminohexane is dissolved in 60 ml dry chloroform and 0.85 ml (6.1 mmol) triethylamine is added.
To this solution is added dropwise 1 g (4.1 mmol) [2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON) dissolved in 20 ml dry chloroform.
This solution is stirred 7 hr, filtered and the filtrate evaporated to an oil.
This oil is vacuum distilled to remove the excess 1,6-diaminohexane.
The residue in the distillation flask is dissolved in acetone and purified on a silica gel chromatography column (eluted with acetone) to give 0.68 g (77percent) of N-(t-butoxycarbonyl)-1,6-diaminohexane as a yellow oil.
Reference: [1] Patent: US5021571, 1991, A,
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Reference: [1] Phytochemistry, 2003, vol. 63, # 3, p. 315 - 334
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
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Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1510 - 1514
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Reference: [1] Phytochemistry, 2003, vol. 63, # 3, p. 315 - 334
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Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1510 - 1514
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Reference: [1] Synthesis, 1982, # 5, p. 404 - 405
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Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4457 - 4478
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Reference: [1] Journal of Organic Chemistry, 1978, vol. 43, # 11, p. 2285 - 2286
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