Phenylacetaldehyde → (6-Phenethylaminohexyl)-carbamic acid tert-butyl ester

HRID 749405Notes

Reaction equation

HRID 749405 reaction equation
Cl.[C:2]([O:6][C:7](=[O:16])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])([CH3:5])([CH3:4])[CH3:3].[C:17]1([CH2:23][CH:24]=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>ClCCl.CO.ClCCl.O>[C:2]([O:6][C:7](=[O:16])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:24][CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 998PhenylacetaldehydeHCID 516892Sodium BicarbonateHCID 3017638tert-Butyl (6-aminohexyl)carbamate monohydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 69233777(6-Phenethylaminohexyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

(6-Aminohexyl)carbamic acid tert-butyl ester hydrochloride (5 g, 20 mmol) was dissolved in 50% dichloromethane/methanol (50 mL) and treated at ambient temperature with phenylacetaldehyde (2.3 mL, 20 mmol) for one hour. Sodium cyanoborohydride (1.2 g, 19 mmol) was added and the mixture stirred overnight. Water was added, followed by saturated sodium hydrogencarbonate and additional dichloromethane. The mixture was partitioned, the organics dried over sodium sulfate and the volatiles removed under reduced pressure to give the title intermediate, which was used without further purification.

Workup

  1. customThe mixture was partitioned
  2. dry with materialthe organics dried over sodium sulfate
  3. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-a1c35eade3814a6aa3ee640dcd44d1a7
Source dataset
uspto-grants-2008_07
Patent number
US07402673B2

Reaction notes

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