Ethanol → HCID 18956198, compound

HRID 2379726Notes

Reaction equation

HRID 2379726 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:16]([O:18]CC)=[O:17])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].C(O)C.[OH-].[Na+]>O.C(O)(=O)C>[C:21]1([C:13]2([C:16]([OH:18])=[O:17])[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:15][CH2:14]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18956195Ethyl 4-phenyl-1-(3-phenylpropyl)piperidine-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18956198HCID 18956198, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

9.3 g Ethyl 1-(3-phenylpropyl)-4-phenyl-4-piperidine-carboxylate (Formula I: R1 =hydrogen, R2 =COOEt, X=Y=CH2), prepared according to the procedure described in U.S. Pat. No. 2,914,532, incorporated herein by reference, was taken up in 35 ml water and 12 ml ethanol with 2.3 g sodium hydroxide, then refluxed for 24 hours and stirred at room temperature for the next two days. The product mixture was poured into water, the solution was acidified with acetic acid, and a precipitate appeared. The precipitate was washed well with water. The product was recrystallized from 4 liters of water and was washed with water, ethanol and ether, yielding 4-phenyl-1-(3-phenylpropyl)-4-piperidinecarboxylic acid, as a white powder, which was used without further purification in the next preparation.

Workup

  1. washThe precipitate was washed well with water
  2. customThe product was recrystallized from 4 liters of water
  3. washwas washed with water, ethanol and ether

Sources & evidence

ORD record
ord-9159b6ca08bd44ceb9d2ebc3645b7f8b
Source dataset
uspto-grants-1994_11
Patent number
US05364867

Reaction notes

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