Dimethylformamide → Benzyl N-(4-aminobutyl)carbamate

HRID 1080835Notes

Reaction equation

HRID 1080835 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 5N NaOH, (clear solution) and stirred for 2 hr. The reaction mixture was acidified to pH=1.25, extracted with ether (2×), made basic (pH>10) with 5N NaOH, and extracted with dichloromethane (2×). The dichloromethane fractions were combined and washed with water (2×), 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×)
  2. extractionextracted with dichloromethane (2×)
  3. washwashed with water (2×)
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9869dbbdcead438898d9a8f91f676ab3
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

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