Hydrochloric Acid → HCID 178479248, compound

HRID 1657568Notes

Reaction equation

HRID 1657568 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([NH:16]C(=O)C)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[ClH:20]>CO>[ClH:20].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178474954HCID 178474954, compound

Product 1

HCID 178479248HCID 178479248, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.25 g. of trans N-[4-(p-nitrophenyl)cyclohexyl]acetamide (prepared as in Example 81) in 50 ml. of hydrochloric acid and 50 ml. of methanol is heated at reflux for about 72 hours. The bulk of the methanol is then removed under vacuum and the residue dissolved in 100 ml. of hot water. The solution is then made strongly basic and extracted with ether and the organic layer then evaporated to dryness to give trans 4-(p-nitrophenyl)cyclohexylamine (I). The residue is dissolved in a small amount of ether which is then treated with 4.9 g. hydrochloric acid in ether to give 4.78 g. (99% yield) of trans N-4-(p-nitrophenyl)cyclohexylamine hydrochloride (I). The analytical sample has a melting point of 293° to 294° C.

Workup

  1. temperatureat reflux for about 72 hours
  2. customThe bulk of the methanol is then removed under vacuum
  3. dissolutionthe residue dissolved in 100 ml
  4. extractionextracted with ether
  5. customthe organic layer then evaporated to dryness

Sources & evidence

ORD record
ord-f0dc86981aef4c6eb023fcdac96640fb
Source dataset
uspto-grants-1976_06
Patent number
US03960961

Reaction notes

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