N-Methylcyclohexylamine → HCID 20318945, compound

HRID 371860Notes

Reaction equation

HRID 371860 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:16]([CH2:17]Br)=[CH:15][C:14]=1[C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:11])[CH3:10]>C(Cl)(Cl)Cl>[C:9]([NH:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:2]([CH:3]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH3:1])=[CH:15][C:14]=1[C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 18629983HCID 18629983, compound

Product 1

HCID 20318945HCID 20318945, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

48 gm of N-methyl-cyclohexylamine were added to 56 gm of 4-acetylamino-3-tert.butyl-benzyl bromide in 500 ml of chloroform, and the mixture was refluxed for 1.5 hours. Subsequently, the reaction mixture was extracted three times with water, and the organic phase was evaporated. The residue was purified column-chromatograhically on silicagel with chloroform/methanol (5:1), and 4-acetylamino-3-tert.butyl-N-cyclohexyl-N-methyl-benzylamine hydrochloride, m.p. 240-243° C (decomp.), was crystallized from a solution of the purified base in absolute ethanol/ether by addition of absolute ethanolic hydrochloric acid.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. extractionSubsequently, the reaction mixture was extracted three times with water
  3. customthe organic phase was evaporated
  4. customThe residue was purified column-chromatograhically on silicagel with chloroform/methanol (5:1), and 4-acetylamino-3-tert.butyl-N-cyclohexyl-N-methyl-benzylamine hydrochloride, m.p. 240-243° C (decomp.)
  5. customwas crystallized from a solution of the purified base in absolute ethanol/ether by addition of absolute ethanolic hydrochloric acid

Sources & evidence

ORD record
ord-aadb56c5e4c24642b713e05e462191a6
Source dataset
uspto-grants-1978_05
Patent number
USRE029628

Reaction notes

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