Water → Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

HRID 465139

Reaction equation

HRID 465139 reaction equation
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26].O>O1CCCC1.CO>[CH2:1]([O:8][C:9]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 199606-Amino-1-hexanolHCID 83172Benzyl succinimido carbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 32 g of N-benzyloxycarbonyloxysuccinimide in 100 ml of tetrahydrofuran is reacted with 15 g of 6-amino-1-hexanol in 30 ml of 50% methanol:tetrahydrofuran. The reaction mixture is stirred overnight at room temperature, and poured into water. The resulting mixture is extracted with methylene chloride and the organic layer is washed with sodium chloride solution, dried over anhydrous magnesium sulfate. The magnesium sulfate is filtered and the solvent is removed by evaporation. The product is recrystallized from ethyl acetate/ether to provide N-(benzyloxycarbonyl)-6-amino-1-hexanol, mp 81.5°-83° C. having the following formula: ##STR32##

Workup

  1. extractionThe resulting mixture is extracted with methylene chloride
  2. washthe organic layer is washed with sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe magnesium sulfate is filtered
  5. customthe solvent is removed by evaporation
  6. customThe product is recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-adac9afde4b44914890d098de66957e8
Source dataset
uspto-grants-1985_10
Patent number
US04550163

Linked notes

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