Hydrochloric Acid → HCID 45261616, compound

HRID 249452Notes

Reaction equation

HRID 249452 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:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][CH3:32])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH3:24])[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:36]CCl>C(O)C>[ClH:36].[CH2:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][CH3:32])=[CH: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)[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54199498HCID 54199498, compound

Product 1

HCID 45261616HCID 45261616, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-[2-[[2,2-bis(2-Ethylphenyl)ethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester (1.20 g, 0.00275 mol) (prepared as described in Method D) was dissolved in ethanol (10 ml) and 12 N sodium hydroxide solution (0.7 ml) was introduced. After stirring the solution at room temperature for 5 h, 37% hydrochloric acid solution was added until the pH was measured as ca. 1. Dichloromethane (250 ml) was introduced, and the mixture was dried (Na2SO4), filtered and evaporated to a residue, which was co-evaporated with acetone. Recrystallization from acetone provided the title compound (0.85 g, 70%) as a white solid, m.p. 205°-206°.

Workup

  1. dry with materialthe mixture was dried (Na2SO4)
  2. filtrationfiltered
  3. customevaporated to a residue, which
  4. customRecrystallization from acetone

Sources & evidence

ORD record
ord-191da13d018c497187fae170ff79b99f
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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