Hydrochloric Acid → HCID 67713573, compound

HRID 1451498Notes

Reaction equation

HRID 1451498 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][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:32]CCl>C(O)C>[ClH:32].[CH2:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54112458(R)-1-(2-(2-benzylbenzyloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 67713573HCID 67713573, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.8 g, 2.1 mmol) was dissolved in ethanol (10 ml) and 2N sodium hydroxide (3.1 ml) was added. The mixture was stirred at ambient temperature overnight. Excess concentrated hydrochloric acid was added followed by dichloromethane. The mixture was concentrated in vacuo and water and dichloromethane was added. The phases were separated and the organic phase was dried (MgSO4). The solvent was evaporated in vacuo to give a foamy residue which was re-evaporated with dichloromethane to give 0.65 g of the title compound as an amorphous solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo and water and dichloromethane
  2. additionwas added
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customto give a foamy residue which
  7. customwas re-evaporated with dichloromethane

Sources & evidence

ORD record
ord-249c9da0bef64eb8847c73ed2a08db3c
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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