Benzyl chloroformate → Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

HRID 376105

Reaction equation

HRID 376105 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19].C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH2:1]([O:8][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 199606-Amino-1-hexanolHCID 516892Sodium Bicarbonate

Product 1

HCID 4184071Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

7.06 ml (47 mmol) of chloroformic acid benzyl ester are added dropwise to a solution of 5.52 g (47 mmol) of 6-aminohexan-1-ol and 3.95 g (47 mmol) of sodium hydrogen carbonate in 100 ml of acetone and 50 ml of water. The mixture is stirred at room temperature for 18 hours and concentrated to approximately 70 ml, and the white precipitate is filtered off, washed with approximately 20 ml of water, taken up in 250 ml of methylene chloride and dried over magnesium sulfate; the magnesium sulfate is filtered off and the residue is concentrated to dryness by evaporation. 6-(N-benzyloxycarbonylamino)hexan-1-ol is obtained in the form of white crystals having a melting point of 58°-60°.

Workup

  1. concentrationconcentrated to approximately 70 ml
  2. filtrationthe white precipitate is filtered off
  3. washwashed with approximately 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationthe magnesium sulfate is filtered off
  6. concentrationthe residue is concentrated to dryness by evaporation

Sources & evidence

ORD record
ord-936b247750754cecb261202c8f1c2d6c
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Linked notes

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