Methyl 4-fluorobenzoate → HCID 71192981, compound

HRID 1427005Notes

Reaction equation

HRID 1427005 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[N:12]1([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1>CS(C)=O.O.C(OCC)(=O)C>[N:12]1([CH:17]2[CH2:22][CH2:21][N:20]([C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=3)[CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 2

HCID 67878Methyl 4-fluorobenzoateHCID 787034-(1-Pyrrolidinyl)piperidine

Product 1

HCID 71192981HCID 71192981, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

Commercially available methyl 4-fluorobenzoate (1.5 g, 9.73 mmol) was added to a solution of commercially available 4-(1-pyrrolidinyl)piperidine (3.0 g, 19.5 mmol) in dimethylsulfoxide (15 mL) at room temperature and then the mixture was stirred under nitrogen atmosphere and under irradiation with microwave at 150° C. for 4 hours. The reaction liquid was allowed to stand to cool to room temperature and then diluted with water and ethyl acetate. The organic layer was washed with water and then dried by a conventional method. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1) to obtain the title compound (2.06 g, 73%).

Workup

  1. customThe reaction liquid
  2. temperatureto cool to room temperature
  3. washThe organic layer was washed with water
  4. customdried by a conventional method
  5. customThe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under vacuum
  7. customThe residue was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3994e8c175274250b037d82885bc0203
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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