Ethyl 4-{4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl}-alpha,alpha-dimethylbenzeneacetate hydrochloride → ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetate HCl

HRID 126829Notes

Reaction equation

HRID 126829 reaction equation
[ClH:1].[OH:2][C:3]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:28])([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)=[O:14])[CH2:6][CH2:5]1>C(O)C.CO.[Pt]=O>[ClH:1].[OH:2][C:3]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:27])([CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)[OH:14])[CH2:6][CH2:5]1

Participants

5

Reactant 1

HCID 12939646Ethyl 4-{4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl}-alpha,alpha-dimethylbenzeneacetate hydrochloride

Product 1

HCID 12939645ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha,alpha-dimethylbenzeneacetate HCl

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 5.64 g (0.01 mole) of ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetate hydrochloride in 200 ml of absolute ethanol and 50 ml of methanol and 0.5 g of platinum oxide is hydrogenated at about 50 psi for about 1 hour until the infrared showed no evidence of a ketone carbonyl function. The solution is filtered and the filtrate concentrated leaving a residue which is recrystallized from butanone and methanol-butanone to give ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetate HCl, M.P. 185°-187° C.

Workup

  1. filtrationThe solution is filtered
  2. concentrationthe filtrate concentrated
  3. customleaving a residue which
  4. customis recrystallized from butanone and methanol-butanone

Sources & evidence

ORD record
ord-fdf206ba5d734f3386754dc20e9f81a9
Source dataset
uspto-grants-1981_03
Patent number
US04254129

Reaction notes

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