Hydrochloric Acid → (r)-n-(2-(3,3-Diphenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

HRID 1614797Notes

Reaction equation

HRID 1614797 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:33]CCl>C(O)C>[ClH:33].[C:24]1([CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10668415(R)-N-(2-(3,3-Diphenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 24842619(r)-n-(2-(3,3-Diphenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ester prepared in Example 13 (0.9 g, 2.3 mmol) was dissolved in ethanol (10 ml) and a 12 N sodium hydroxide solution (0.6 ml) was added. The reaction mixture was stirred at room temperature for 4 h. Concentrated hydrochloric acid solution (0.7 ml) was added with cooling of the reaction vessel in an ice-bath and dichloromethane (300 ml) was added. The resulting emulsion was dried over sodium sulphate and the solvent evaporated in vacuo to give an oily residue which was crystallised from acetone. This afforded 0.5 g (54%) of the title compound.

Workup

  1. temperaturewith cooling of the reaction vessel in an ice-bath
  2. dry with materialThe resulting emulsion was dried over sodium sulphate
  3. customthe solvent evaporated in vacuo
  4. customto give an oily residue which
  5. customwas crystallised from acetone

Sources & evidence

ORD record
ord-5623f5e801d84c5c886b0c932856880a
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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