Sodium Hydroxide → 2-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

HRID 126835Notes

Reaction equation

HRID 126835 reaction equation
Cl.[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]CC)=[O:23])=[CH:17][CH:16]=2)=[O:14])[CH2:6][CH2:5]1.[OH-].[Na+]>CO>[OH:2][C:3]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=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]([OH:24])=[O:23])=[CH:17][CH:16]=2)=[O:14])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12939646Ethyl 4-{4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl}-alpha,alpha-dimethylbenzeneacetate hydrochloride

Product 1

HCID 99356992-(4-(4-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1 g of ethyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetate hydrochloride, 25 ml of methanol and 5 ml of 25% sodium hydroxide solution is stirred and refluxed for 2 hours then concentrated to a solid, neutralized with dilute hydrochloric acid and extracted with hot toluene. The toluene extract is filtered and concentrated to a residue which is recrystallized from chloroform/toluene to give 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationthen concentrated to a solid, neutralized with dilute hydrochloric acid
  3. extractionextracted with hot toluene
  4. extractionThe toluene extract
  5. filtrationis filtered
  6. concentrationconcentrated to a residue which
  7. customis recrystallized from chloroform/toluene

Sources & evidence

ORD record
ord-dea4c104e3314715b4d28c650a53f49a
Source dataset
uspto-grants-1981_03
Patent number
US04254130

Reaction notes

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