Hydrochloric Acid → HCID 178479228, compound

HRID 1605532Notes

Reaction equation

HRID 1605532 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)#[N:2].O.N.[ClH:14]>[Ni].CO>[ClH:14].[NH2:2][CH2:1][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12896473Azane;hydrateHCID 178511260HCID 178511260, compound

Product 1

HCID 178479228HCID 178479228, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In order to carry out the reaction advantageously on an industrial scale, trans-4-cyanocyclohexane-1-carboxylic acid is hydrogenated at a room temperature under pressure in a hydrous methanol made alkaline by the addition of ammonia water in the presence of Raney nickel, and then the catalyst is filtered and the solvent is removed by distillation. When lower alkyl trans-4-cyanocyclohexane-1-carboxylate is used as a starting material, it is subjected to the same reaction and treatment as above, and the residue is hydrolyzed with dilute hydrochloric acid in a hot water bath to produce trans-4-aminomethyl-cyclohexane-1-carboxylic acid hydrochloride. The reaction solution is passed through a column of a weakly basic ion-exchange resin to obtain trans-4-aminomethylcyclohexane-1-carboxylic acid in an yield of from 85 to 95 percent.

Workup

  1. filtrationthe catalyst is filtered
  2. customthe solvent is removed by distillation
  3. customis subjected to the same reaction and treatment as above, and the residue

Sources & evidence

ORD record
ord-3c0254deb83146e4a5d06707ac44f660
Source dataset
uspto-grants-1976_04
Patent number
US03950405

Reaction notes

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