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

HRID 35247
Notes
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Reaction equation

HRID 35247 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 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 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-d3926ad918984844bf5b7332cf93bba8
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766120

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes