Cyclohexylamine → 5-Chloro-N-cyclohexylpentanamide

HRID 2235228Notes

Reaction equation

HRID 2235228 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14]>ClCCl>[CH:1]1([NH:7][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][Cl:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 740895-Chlorovaleryl chloride

Product 1

HCID 116729745-Chloro-N-cyclohexylpentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve cyclohexylamine (8.86 mL, 77.5 mmol) in dichloromethane (700 mL), cool to 0° C. and add 5-chloropentanoyl chloride (10 mL, 77.5 mmol). After 6 h, wash the mixture with 1N HCl and saturated aqueous sodium bicarbonate and brine, dry the organic layer over sodium sulfate and evaporate to a white solid to obtain 5-chloro-pentanoic acid cyclohexylamide: MS (EI) m/z=217 (M+).

Workup

  1. washwash the mixture with 1N HCl and saturated aqueous sodium bicarbonate and brine
  2. dry with materialdry the organic layer over sodium sulfate
  3. customevaporate to a white solid

Sources & evidence

ORD record
ord-078c6d8343cb49738fb84e11503d4461
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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