Water → HCID 70230009, compound

HRID 1460671Notes

Reaction equation

HRID 1460671 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:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:7]1)=[O:5])C.[OH-].[Na+].O>C(O)C>[ClH:30].[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[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

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70230357HCID 70230357, compound

Product 1

HCID 70230009HCID 70230009, compoundYield 165.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-[2-[[2-(2-Chlorophenyl)-2-(2-methylphenyl)ethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester (4.1 g, 0.0096 mol) (prepared as described in Method D) was dissolved in ethanol (100 ml) and 18N sodium hydroxide solution (10 ml) was introduced. After stirring the solution at room temperature for 1 h water (500 ml) was added, and the solution was washed with diethyl ether (2×100 ml). The pH of the aqueous phase was adjusted to 1 using 2N hydrochloric acid solution and extracted with dichloromethane (4×200 ml). The combined extracts were dried (MgSO4), evaporated and the residue was crystallized from toluene/trace methanol to provide the title compound (3.47 g, 87%) as a white crystalline solid, m.p. 231°-234°.

Workup

  1. additionwas added
  2. washthe solution was washed with diethyl ether (2×100 ml)
  3. extractionextracted with dichloromethane (4×200 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customthe residue was crystallized from toluene/trace methanol

Sources & evidence

ORD record
ord-cb8c2a8eae59423891c54516de75dbd3
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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