N-Methylcyclohexylamine → HCID 20319151, compound

HRID 866950Notes

Reaction equation

HRID 866950 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]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([Cl:25])=[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]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([Cl:25])=[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 20319077HCID 20319077, compound

Product 1

HCID 20319151HCID 20319151, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

26 gm of N-methyl-cyclohexylamine were added to 29 gm of 2-acetylamino-4-tert.butyl-5-chloro-benzyl bromide in 1.5 liters of carbon tetrachloride, and the mixture was refluxed for 2 hours. After cooling, the precipitated N-methyl-cyclohexylamine hydrobromide was filtered off, and the filtrate was evaporated. The residue was taken up in 2 N acetic acid, the solution was extracted with chloroform, and the acid phase was made alkaline with concentrated ammonia, extracted three times with chloroform, and the organic phase was evaporated. After column-chromatographic purification on silicagel with ethyl acetate/chloroform (1:1), the 2-acetylamino-4-tert.butyl-5-chloro-N-cyclohexyl-N-methylbenzylamine thus obtained was crystallized from absolute ethanol and recrystallized from ethanol, whereupon it had a melting point of 174°-175.5° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated N-methyl-cyclohexylamine hydrobromide was filtered off
  4. customthe filtrate was evaporated
  5. extractionthe solution was extracted with chloroform
  6. extractionextracted three times with chloroform
  7. customthe organic phase was evaporated
  8. customAfter column-chromatographic purification on silicagel with ethyl acetate/chloroform (1:1)

Sources & evidence

ORD record
ord-6430103ef577431bbcee6fe7ce8098ef
Source dataset
uspto-grants-1978_07
Patent number
US04101671

Reaction notes

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