N-Methylcyclohexylamine → HCID 20318945, compound

HRID 866952Notes

Reaction equation

HRID 866952 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-chromatography 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-chromatography 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-5eb86be7e49a4f0aa175410267a393d8
Source dataset
uspto-grants-1978_07
Patent number
US04101671

Reaction notes

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