Dimethylformamide → Benzyl N-(4-aminobutyl)carbamate

HRID 1599696Notes

Reaction equation

HRID 1599696 reaction equation
Cl.Cl.[CH2:3]([NH2:8])[CH2:4][CH2:5][CH2:6][NH2:7].CN(C=O)C.[C:14](Cl)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[OH-].[Na+]>O>[NH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:8][C:14](=[O:15])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9532Putrescine DihydrochlorideHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 2783677Benzyl N-(4-aminobutyl)carbamateYield 46.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,4-butanediamine dihydrochloride (5.96 g, 37 mmol) was dissolved in water (15 mL), and DMF (50 mL) was added. With rapid stirring, CBZ-Cl (1.0 mL, 7.0 mmol) was added dropwise over 2 minutes. The cloudy solution had pH~2.8. The pH was adjusted to 9.0 with 5 N NaOH, (clear solution) and stirred for 2 hr. 10 The reaction mixture was acidified to pH=1.25, extracted with ether (2 X), made basic (pH>10) with 5 N NaOH, and extracted with dichloromethane (2 X). The dichloromethane fractions were combined and washed with water (2 X), dried and evaporated in vacuo to provide the crude mono-CBZ amine (0.72 g, 3.24 mmol, 46%) which was used as is in the next step.

Workup

  1. extractionextracted with ether (2 X)
  2. extractionextracted with dichloromethane (2 X)
  3. washwashed with water (2 X)
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9f30a3d9e8ae456c9c19074c529d9f46
Source dataset
uspto-grants-1998_04
Patent number
US05741792

Reaction notes

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