Hydrochloric Acid → 1-(2-(3-Phenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

HRID 1451496Notes

Reaction equation

HRID 1451496 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:27]CCl>C(O)C>[ClH:27].[C:18]1([CH2:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 539871951-(2-(3-Phenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 677135711-(2-(3-Phenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (3.2 g, 10 mmol) was dissolved in ethanol (10 ml) and 12N sodium hydroxide (2.5 ml) was added. The mixture was stirred at ambient temperature for 3 h. Excess concentrated hydrochloric acid was added followed by dichloromethane (300 ml). The mixture was dried (Na2SO4) and the solvent was evaporated in vacuo to give a residue which was re-evaporated twice with acetone. Crystallisation of the residue from a mixture of acetone and ethyl acetate followed by recrystallisation from acetone gave 1.1 g of the title compound as a solid.

Workup

  1. dry with materialThe mixture was dried (Na2SO4)
  2. customthe solvent was evaporated in vacuo
  3. customto give a residue which
  4. customwas re-evaporated twice with acetone
  5. customCrystallisation of the residue
  6. additionfrom a mixture of acetone and ethyl acetate
  7. customfollowed by recrystallisation from acetone

Sources & evidence

ORD record
ord-78e3e1f772e941c0b5981e39cf572d3a
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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