Methanol → HCID 10164785, compound

HRID 279081Notes

Reaction equation

HRID 279081 reaction equation
CO.O1CCOCC1.[OH:9][C:10]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[O:42][CH2:43][CH2:44][CH2:45][O:46]C(=O)C)[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:12][CH2:11]1.[OH-].[Na+]>O>[OH:9][C:10]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[O:42][CH2:43][CH2:44][CH2:45][OH:46])[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 10144259HCID 10144259, compound

Product 1

HCID 10164785HCID 10164785, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a liquid mixture of 5 mL of methanol and 5 mL of dioxane was dissolved 180 mg (0.32 mmol) of 4-(4-hydroxy-4-(2-(3-acetoxypropoxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide. To the resulting solution, 5 mL of a 1N aqueous solution of sodium hydroxide was added. The resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with chloroform, washing with water and drying. The residue obtained by distilling off the solvent was purified by chromatography on a silica gel column, whereby 150 mg (yield: 89.8%) of 4-(4-hydroxy-4-(2-(3-hydroxypropoxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 25) was obtained.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washwashing with water
  3. customdrying
  4. customThe residue obtained
  5. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-8acbad2885b740f0b905977fce790cd6
Source dataset
uspto-grants-2002_03
Patent number
US06362203B1

Reaction notes

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