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

HRID 249433Notes

Reaction equation

HRID 249433 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-piperidine carboxylic acid ethyl ester (example 1) (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. Dichloromethane (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, m.p. 210°-216° C.

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-3e39e5fabf6d40d5ad3f4d031d2f864d
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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