Hydrochloric Acid → (R)-1-(2-((2,2-Diphenylethenyl)oxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

HRID 566564Notes

Reaction equation

HRID 566564 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][CH:15]=[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:32]CCl>C(O)C>[ClH:32].[C:23]1([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH: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:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10621814(R)-1-(2-((2,2-Diphenylethenyl)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 24842617(R)-1-(2-((2,2-Diphenylethenyl)oxy)ethyl)-3-piperidinecarboxylic acid hydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-(2-((2,2-Diphenylethenyl)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (Example 50) (3.0 g, 0.079 mol) was dissolved in ethanol (20 ml) and 12 N sodium hydroxide solution (2.0 ml) was introduced. After stirring the solution at room temperature for 2.5 h, 37% hydrochloric acid (ca. 2.2 ml) was added, with acidity measured at pH 2. Dichloro-methane (300 ml) was introduced, and the mixture was dried (MgSO4). Filtration and evaporation of the filtrate gave a solid, which was triturated with diethyl ether, to give the title compound (2.65 g, 86%) as a white solid.

Workup

  1. dry with materialthe mixture was dried (MgSO4)
  2. filtrationFiltration and evaporation of the filtrate
  3. customgave a solid, which
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-b71c7722f460403680d98bc5ccff6818
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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