Ammonium Hydroxide → Phenylamino-1-(2-phenylethyl)-4-piperidinecarboxylic acid

HRID 1973791Notes

Reaction equation

HRID 1973791 reaction equation
C1(N[C:8]2([C:22]([O:24]CC3C=CC=CC=3)=[O:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)C=CC=CC=1.[OH-].[NH4+:33]>[Pd].CO>[C:16]1([NH:33][CH:10]2[CH2:9][CH:8]([C:22]([OH:24])=[O:23])[CH2:13][CH2:12][N:11]2[CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 12298150Phenylmethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

Product 1

HCID 86734310Phenylamino-1-(2-phenylethyl)-4-piperidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 60 parts of phenylmethyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate and 320 parts of methanol is hydrogenated at normal pressure and at room temperature with 10 parts of palladium-on-charcoal catalyst 10%. Upon the addition of a concentrated ammonium hydroxide solution, the precipitate, which is formed during the hydrogenation, is dissolved. The catalyst is filtered off and the filtrate is concentrated. Methanol is added and the whole is concentrated again. After cooling to room temperature the product is filtered off and dried in vacuo at 120° C, yielding 43.7 parts of 4-(phenylamino-1-(2-phenylethyl)-4-piperidinecarboxylic acid; mp. 268° C.

Workup

  1. customthe precipitate, which is formed during the hydrogenation
  2. dissolutionis dissolved
  3. filtrationThe catalyst is filtered off
  4. concentrationthe filtrate is concentrated
  5. additionMethanol is added
  6. concentrationthe whole is concentrated again
  7. filtrationis filtered off
  8. customdried in vacuo at 120° C

Sources & evidence

ORD record
ord-c6692313b7da4e0aa778971ac01cf6cb
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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