Potassium Carbonate → [4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]methyl-propanedioic acid, dimethyl ester

HRID 1581855Notes

Reaction equation

HRID 1581855 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[N:29]1[CH:34]=[CH:33][C:32]([C:35]([OH:48])([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:31][CH:30]=1>O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[OH:48][C:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH:32]1[CH2:33][CH2:34][N:29]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:30][CH2:31]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolHCID 86585530[4-(4-Chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester

Product 1

HCID 86585531[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]methyl-propanedioic acid, dimethyl esterYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix together [4-(4-chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester (300 mg, 0.92 mmol), potassium carbonate (350 mg, 2.5 mmol), α-(4-pyridyl)benzhydrol (500 mg, 1.9 mmol), water (3 mL) and toluene (7 mL). Heat the mixture to reflux. After 5 days, cool to room temperature. Add ethyl acetate and water. Wash the organic phase with brine, dry over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent) to give the title compound (387 mg, 76%).

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. washWash the organic phase with brine
  4. dry with materialdry over anhydrous magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent)

Sources & evidence

ORD record
ord-410a594a48584ee9a43bdc751f031924
Source dataset
uspto-grants-2004_05
Patent number
US06730791B2

Reaction notes

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