Sodium Carbonate → 4-[4-(2-hydroxyphenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenyl-N,N-dimethylbutanamide

HRID 279080Notes

Reaction equation

HRID 279080 reaction equation
[Br-].[CH3:2][N+:3]([CH3:21])=[C:4]1[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][O:5]1.[OH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[OH:35][C:29]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[OH:22])[CH2:30][CH2:31][N:32]([CH2:6][CH2:7][C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]([N:3]([CH3:2])[CH3:21])=[O:5])[CH2:33][CH2:34]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2723589(Dihydro-3,3-diphenyl-3H-furan-2-ylidene)dimethylammonium bromideHCID 111062194-(2-Hydroxyphenyl)piperidin-4-ol

Product 1

HCID 102263704-[4-(2-hydroxyphenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenyl-N,N-dimethylbutanamideYield 78.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In 20 mL of anhydrous dimethylformamide were dissolved 3.5 g (10 mmol) of dimethyl(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide and 1.93 g (10 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 3.2 g (30 mmol) of sodium carbonate, followed by stirring at 80° C. for 1.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent and the residue thus obtained was dissolved in ethyl acetate. The resulting solution was washed with water and dried. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 3.6 g (yield: 78.6%) of 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 1) was obtained.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customthe residue thus obtained
  4. washThe resulting solution was washed with water
  5. customdried
  6. customThe residue obtained
  7. concentrationby concentrating the solvent under reduced pressure
  8. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-8e90fd56c3f347a3b2d80af58e672b27
Source dataset
uspto-grants-2002_03
Patent number
US06362203B1

Reaction notes

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