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

HRID 978019Notes

Reaction equation

HRID 978019 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 and aqueious saturated potassium carbonate solution, 10% 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 mmHg.

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 and aqueious saturated potassium carbonate solution, 10% 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-f2e6e344cebd4de4bcd21ac08395917a
Source dataset
uspto-grants-1987_05
Patent number
US04663323

Reaction notes

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