Hydrochloric Acid → Benzyl N-(4-hydroxybutyl)carbamate

HRID 1368876Notes

Reaction equation

HRID 1368876 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[OH-].[Na+].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].Cl>O>[CH2:13]([O:12][C:10]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformate2×HCID 14798Sodium Hydroxide2×HCID 258684-Amino-1-butanol

Product 1

HCID 3366758Benzyl N-(4-hydroxybutyl)carbamateYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-1-butanol (5 g) was dissolved in water (50 ml) and cooled to 0° C. The solution was added with 1 N aqueous sodium hydroxide (56.1 ml) and then with benzyl chloroformate (8 ml) and stirred at room temperature for 23 hours. 5 N aqueous sodium hydroxide (22.4 ml) and benzyl chloroformate (16 ml) were further added to the mixture, and stirring was continued for 2 hours. The reaction system was cooled to 0° C. and adjusted to pH 4 with 5 N hydrochloric acid, and the organic substances were extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the precipitated crystals were washed with diethyl ether to obtain 4-benzyloxycarbonylamino-1-butanol (8.15 g, 65%).

Workup

  1. temperatureThe reaction system was cooled to 0° C.
  2. extractionthe organic substances were extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. washthe precipitated crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-147d062677ea480782d6efa14773c07b
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

Loading…