Sodium Hydroxide → HCID 53973983, compound

HRID 1614835Notes

Reaction equation

HRID 1614835 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]([CH3:30])[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>[CH3:30][C:26]1[CH:25]=[C:24]([C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=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 54527806HCID 54527806, compound

Product 1

HCID 53973983HCID 53973983, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N-(2-(3-(3-Methylphenyl)-3-phenyl-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (3.5 g, 8.6 mmol) was dissolved in 96% ethanol (10 ml) and a 12 N sodium hydroxide solution (2.2 ml) was added. The reaction mixture was stirred at room temperature for 4 h. The solvent was evaporated in vacuo and dichloromethane (100 ml) and water (10 ml) were added. A concentrated hydrochloric acid solution (3.4 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 to approx. 10 ml in vacuo. Dichloromethane (250 ml) and water (40 ml) were added and pH of the solution was adjusted to 8.5 with a 4 N sodium hydroxide solution. The phases were separated and the organic phases was dried over sodium sulphate. The solvent was evaporated in vacuo to give 2.4 g (74%) of the title compound.

Workup

  1. customThe solvent was evaporated in vacuo and dichloromethane (100 ml) and water (10 ml)
  2. additionwere added
  3. additionA concentrated hydrochloric acid solution (3.4 ml) was added
  4. temperaturewith cooling on an ice-bath
  5. customThe phases were separated and from the organic phase the solvent
  6. customwas 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. additionDichloromethane (250 ml) and water (40 ml) were added
  10. customThe phases were separated
  11. dry with materialthe organic phases was dried over sodium sulphate
  12. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1988e5a6e0d44603b88c489bf7cdb2fb
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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