Hydrochloric Acid → HCID 178479248, compound
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
Product 1
Reagents, catalysts & solvents 1
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.