Benzene → N,2-dicyclohexylacetamide

HRID 917940Notes

Reaction equation

HRID 917940 reaction equation
[CH:1]1([CH2:7][C:8](Cl)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC=CC=1.[CH:17]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(Cl)Cl>[CH:17]1([NH:23][C:8](=[O:9])[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 241Benzene2×HCID 7965CyclohexylamineHCID 2757989Cyclohexylacetyl chloride

Product 1

HCID 880907N,2-dicyclohexylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N-cyclohexylcyclohexaneacetamide is prepared from cyclohexylacetyl chloride (from 10 gm. of cyclohexylacetic acid and 50 ml. of thionyl chloride, 45 minutes at reflux) in 50 ml. of dry benzene added to 14 gm. of cyclohexylamine in 100 ml. of benzene over ten minutes. The reaction is stirred at reflux for one hour, cooled and diluted with methylene chloride. The organic layer is washed with dilute hydrochloric acid, then water and sodium bicarbonate solution, dried and concentrated. Product is recrystallized from alcohol water: 11.8 gm. (76%), m.p. 164°-165°.

Workup

  1. temperatureat reflux for one hour
  2. temperaturecooled
  3. washThe organic layer is washed with dilute hydrochloric acid
  4. dry with materialwater and sodium bicarbonate solution, dried
  5. concentrationconcentrated
  6. customProduct is recrystallized from alcohol water

Sources & evidence

ORD record
ord-2d593d2bb7a544ffac40bc1b3adc89d3
Source dataset
uspto-grants-1976_07
Patent number
US03968211

Reaction notes

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