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

HRID 2120389Notes

Reaction equation

HRID 2120389 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:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[N:31]1[CH:36]=[CH:35][C:34]([C:37]([OH:50])([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:33][CH:32]=1>O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[OH:50][C:37]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[CH:34]1[CH2:35][CH2:36][N:31]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:32][CH2:33]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolHCID 12132443[4-(4-Chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, diethyl ester

Product 1

HCID 12132444[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]methyl-propanedioic acid, diethyl esterYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix together [4-(4-chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, diethyl ester (380 mg, 1.1 mmol), potassium carbonate (450 mg, 3.2 mmol), α-(4-pyridyl)benzhydrol (500 mg, 1.9 mmol), water (4 mL) and toluene (10 mL). Heat the mixture to reflux. After 7 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 (200 g of silica gel, 10% methanol/chloroform as eluent) to give the title compound (627 mg, 99%).

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 (200 g of silica gel, 10% methanol/chloroform as eluent)

Sources & evidence

ORD record
ord-40ea80d3ee084b3cab3146f995d1d2d1
Source dataset
uspto-grants-2004_02
Patent number
US06689898B2

Reaction notes

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