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Potassium Carbonate → tert-Butyl 4-[4-(3-methoxy-3-oxopropyl)piperidin-1-yl]benzoate

HRID 446559
Notes
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Reaction equation

HRID 446559 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.F[C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:12][O:11][C:9](=[O:10])[CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:14]2[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[CH:16][CH:15]=2)[CH2:2][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2736444Tert-butyl 4-fluorobenzoateHCID 10261546Methyl 3-(piperidin-4-yl)propanoate

Product 1

HCID 86663456tert-Butyl 4-[4-(3-methoxy-3-oxopropyl)piperidin-1-yl]benzoateYield 32.7%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 3-(piperidin-4-yl)propanoate (WO2004/92124 A2) (206 mg, 1.11 mmol) was dissolved in N,N-dimethylformamide (10 mL), tert-butyl 4-fluorobenzoate (141 mg, 1.11 mmol) and potassium carbonate (100 mg, 1.11 mmol) were added, and the mixture was stirred at 120° C. under a nitrogen atmosphere for 16 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate, 10:1, v/v) to give the title compound (126 mg; yield, 31%) as a colorless oily substance.

Workup

  1. customto separate the layers
  2. customThe resulting organic layer was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-42346772ca714dc69f0744d71a88a445
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08476253B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes