Benzyl chloroformate → Benzyl N-(4-aminobutyl)carbamate

HRID 1080837Notes

Reaction equation

HRID 1080837 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]([NH2:7])C.[OH-].[Na+].[C:10](Cl)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>CN(C=O)C.O>[NH2:7][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:10](=[O:11])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 5508801,4-DIAMINOPENTANE

Product 1

HCID 2783677Benzyl N-(4-aminobutyl)carbamateYield 30%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

To a solution of 1,4-diaminopentane (25 g, 155 mmol) in 100 mL DMF/H2O (1:1) was added 5N NaOH to adjust the pH to 9. CBZ-Cl (3.7 mL, 26 mmol) was added as one portion and stirred at room temperature for 16 hrs. The reaction was acidified to pH 1.25 and washed with diethyl ether. The pH of the reaction was then adjusted to 9.5 and the reaction extracted with EtOAc. The organic layer was washed with H2O, brine, dried over Na2SO4 and evaporated to give title compound (1.57 g, 30%).

Workup

  1. washwashed with diethyl ether
  2. extractionthe reaction extracted with EtOAc
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-18adffae53b844c8af0bf7ca9e520e00
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

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