Sodium Hydroxide → HCID 54132308, compound

HRID 1614833Notes

Reaction equation

HRID 1614833 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][CH:16]=[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[Cl:30][C:26]1[CH:25]=[C:24]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH2:15][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:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53674309HCID 53674309, compound

Product 1

HCID 54132308HCID 54132308, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N-(2-(3-(3-Chlorophenyl)-3-phenyl-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (3.0 g, 7.0 mmol) dissolved in 96% ethanol (10 ml) and a 12 N sodium hydroxide solution (1.75 ml) was added. The reaction mixture was stirred at room temperature for 5 h. The solvent was evaporated in vacuo and dichloromethane was added (100 ml). A concentrated hydrochloric acid solution (2.9 ml) was added with cooling on an ice-bath. The phases were separated, and from the organic phase the solvent was evaporated in vacuo. Water (100 ml) was added to the residue and the aqueous solution was washed with small portions of ethyl acetate. The aqueous phase was reduced in vacuo to approx. 50 ml and dichloromethane (250 ml) was added. A 4 N sodium hydroxide solution was added until the pH was measured as 8.3. The phases were separated and the organic phase was dried over sodium sulphate. The solvent was evaporated in vacuo to give 2.7 g (96%) of the title compound.

Workup

  1. customThe solvent was evaporated in vacuo and dichloromethane
  2. additionwas added (100 ml)
  3. additionA concentrated hydrochloric acid solution (2.9 ml) was added
  4. temperaturewith cooling on an ice-bath
  5. customThe phases were separated
  6. customfrom the organic phase the solvent was evaporated in vacuo
  7. additionWater (100 ml) was added to the residue
  8. washthe aqueous solution was washed with small portions of ethyl acetate
  9. additionwas added
  10. additionA 4 N sodium hydroxide solution was added until the pH
  11. customThe phases were separated
  12. dry with materialthe organic phase was dried over sodium sulphate
  13. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7aa8e1788be14a33a4b1419ce094c9a6
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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