Carbon Tetrachloride → HCID 20318966, compound

HRID 866949Notes

Reaction equation

HRID 866949 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([Br:17])=[CH:9][C:6]=1[CH2:7]Br)(=[O:3])[CH3:2].[CH3:18][NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(Cl)(Cl)(Cl)[Cl:27]>>[ClH:27].[C:1]([NH:4][C:5]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([Br:17])=[CH:9][C:6]=1[CH2:7][N:19]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH3:18])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 7514N-MethylcyclohexylamineHCID 20319036HCID 20319036, compound

Product 1

HCID 20318966HCID 20318966, compound

Procedure

A mixture of 25 gm of 2-acetylamino-5-bromo-4-tert.butyl-benzyl bromide, 1.5 liters of carbon tetrachloride and 23 gm of N-methyl-cyclohexylamine was refluxed for 1 hour. After cooling, the precipitated N-methyl-cyclohexylamine hydrobromide was filtered off and the filtrate was evaporated. The residue was admixed with 2 N hydrochloric acid, and the mixture was extracted twice with benzene. The acid phase was made alkaline with concentrated ammonia, extracted three times with chloroform, and the organic phase was dried and evaporated. The residue was purified by column-chromatography on silicagel with ethylacetate/chloroform (1:1), and 2-acetylamino-5-bromo-4-tert.butyl-N-cyclohexyl-N-methylbenzylamine hydrochloride was precipitated from a solution of the purified residue in ethanol/ether with ethanolic hydrochloric acid. The crude product was recrystallized from ethanol-ether, whereupon it had a melting point of 231°-234° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe precipitated N-methyl-cyclohexylamine hydrobromide was filtered off
  4. customthe filtrate was evaporated
  5. extractionthe mixture was extracted twice with benzene
  6. extractionextracted three times with chloroform
  7. customthe organic phase was dried
  8. customevaporated
  9. customThe residue was purified by column-chromatography on silicagel with ethylacetate/chloroform (1:1), and 2-acetylamino-5-bromo-4-tert.butyl-N-cyclohexyl-N-methylbenzylamine hydrochloride
  10. customwas precipitated from a solution of the purified residue in ethanol/ether with ethanolic hydrochloric acid
  11. customThe crude product was recrystallized from ethanol-ether, whereupon it

Sources & evidence

ORD record
ord-752c013d01dc44f684dcd5b69b11cb32
Source dataset
uspto-grants-1978_07
Patent number
US04101671

Reaction notes

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