Isopropanol → Pituxate

HRID 1578588Notes

Reaction equation

HRID 1578588 reaction equation
C(O)(C)C.[OH-].[Na+].[C:7]1([C:13]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH:14]2[C:16]([OH:18])=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[N:26]1([CH2:32][CH2:33]Cl)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>O>[CH2:29]1[CH2:30][CH2:31][N:26]([CH2:32][CH2:33][O:17][C:16]([CH:14]2[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:15]2)=[O:18])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 980712,2-Diphenylcyclopropanecarboxylic acid

Product 1

HCID 65810Pituxate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml. of isopropanol and 0.21 mol of powdered sodium hydroxide are added to a mixture of 0.1 mol of 2,2-diphenyl-cyclopropane-carboxylic acid and 0.11 mol of piperidino-β-chloroethane hydrochloride. The mixture is heated under reflux for 8 hours, 300 ml. of water are added and the mixture extracted with diethyl ether. The ether phase is washed with water, dried over sodium sulphate, and the ether removed in vacuo to yield the base.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 8 hours
  3. extractionthe mixture extracted with diethyl ether
  4. washThe ether phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. customthe ether removed in vacuo
  7. customto yield the base

Sources & evidence

ORD record
ord-428a514c0d1549efa910502bc3c0b6d3
Source dataset
uspto-grants-1976_02
Patent number
US03937832

Reaction notes

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