N-Methylcyclohexylamine → HCID 20319113, compound

HRID 1605583Notes

Reaction equation

HRID 1605583 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:9]([NH:12][C:13]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:14]=1[CH2:15]Br)(=[O:11])[CH3:10]>C(Cl)(Cl)(Cl)Cl>[C:9]([NH:12][C:13]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:14]=1[CH2:15][N:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:1])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 20318965HCID 20318965, compound

Product 1

HCID 20319113HCID 20319113, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

24 gm of N-methyl-cyclohexylamine were added to 23 gm of 2-acetylamino-5-tert.butyl-benzylbromide in 1.6 liters of carbon tetrachloride, and the mixture was refluxed for 1 hour. After cooling, the precipitated N-methyl-cyclohexylamine hydrobromide was filtered off, the filtrate was evaporated, and the crude product was purified chromatographically on silicagel with ethyl acetate. The corresponding fractions were combined and evaporated, and the 2-acetylamino-5-tert.butyl-N-cyclohexyl-N-methyl-benzylamine thus obtained was recrystallized from petroleum ether, whereupon it had a melting point of 111°-112.5°C.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe precipitated N-methyl-cyclohexylamine hydrobromide was filtered off
  4. customthe filtrate was evaporated
  5. customthe crude product was purified chromatographically on silicagel with ethyl acetate
  6. customevaporated

Sources & evidence

ORD record
ord-bd8863a1fbfd4588a5c7abcb4a87b911
Source dataset
uspto-grants-1976_04
Patent number
US03950393

Reaction notes

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