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

HRID 566531Notes

Reaction equation

HRID 566531 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 15 (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 (Na2SO4) 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 (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customto give an oily residue which
  5. customwas crystallised from acetone

Sources & evidence

ORD record
ord-8c2e5678f3914f99b5f347dc7d9de967
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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