Water → HCID 18470387, compound

HRID 2228905Notes

Reaction equation

HRID 2228905 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C(N(C(C)C)CC)(C)C.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.O>ClCCl>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 199606-Amino-1-hexanolHCID 81531Diisopropylethylamine

Product 1

HCID 18470387HCID 18470387, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-amino-1-hexanol (12.9 g) and diisopropylethylamine (11.9 g) in dry dichloromethane (100 ml) at 5° C. was added 4-chlorobenzoyl chloride (16.1 g) in dry dichloromethane at such a rate to maintain the temperature below 10° C. After stirring for 16 h, the mixture was poured into water and filtered. The solid was washed with water, 2M hydrochloric acid (150 ml), water, dichloromethane and was dried under reduced pressure to give 6-(4-chlorobenzoylamino)hexan-1-ol (19.2 g). 1H-NMR (d6-DMSO) δ 1.25-1.65 (8H, m), 3.24 (2H, q), 3.38 (2H, t), 7.52 (2H, m), 7.84 (2H, m) and 8.54 (1H, bt)

Workup

  1. temperatureto maintain the temperature below 10° C
  2. filtrationfiltered
  3. washThe solid was washed with water, 2M hydrochloric acid (150 ml), water, dichloromethane
  4. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-582dcaa940a44be98eea31c4d0a2c91a
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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