N-Methylcyclohexylamine → 4-Chloro-N-cyclohexyl-N-methylbutanamide

HRID 1719575Notes

Reaction equation

HRID 1719575 reaction equation
C(OCC)(=O)C.[CH3:7][NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20].C(N(CC)CC)C>O>[CH3:7][N:8]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][Cl:15]

Participants

6

Reactant 4

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 783704-Chlorobutyryl chloride

Product 1

HCID 132082974-Chloro-N-cyclohexyl-N-methylbutanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl acetate (400 ml) is added N-methylcyclohexylamine (26 ml), and to the mixture are added dropwise with stirring 4-chlorobutyryl chloride (25 ml) and triethylamine (33.5 ml) over a period of 20 minutes with keeping the inner temperature at 10° to 20° C. by ice-cooling. The mixture is further stirred at room temperature for one hour. After the reaction, water is added to the reaction mixture. The organic layer is separated and washed with water an aqueious saturated potassium carbonate solution, 10% aqueous hydrochloric acid and water in order, and then dried over anhydrous sodium sulfate. After filtering off sodium sulfate, the mother liquor is concentrated and distilled under reduced pressure to give N-methyl-N-cyclohexyl-4-chlorobutyramide (41.5 g), b.p. 133°-136° C./2 mm Hg.

Workup

  1. customat 10° to 20° C.
  2. temperaturecooling
  3. additionis added to the reaction mixture
  4. customThe organic layer is separated
  5. washwashed with water an aqueious saturated potassium carbonate solution, 10% aqueous hydrochloric acid and water in order
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtering off sodium sulfate
  8. concentrationthe mother liquor is concentrated
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-e7252266dd6c4cc4b55b7603db78d91b
Source dataset
uspto-grants-1985_09
Patent number
US04540703

Reaction notes

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