Dimethyl Sulfoxide → Ethyl 4-(3-dimethylaminopyrrolidin-1-yl)benzoate

HRID 2069320Notes

Reaction equation

HRID 2069320 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:20])[CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH3:13][N:14]([CH3:20])[CH:15]1[CH2:19][CH2:18][N:17]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 69209289Ethyl 4-(3-dimethylaminopyrrolidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 4-fluorobenzoate (4.47 g), dimethylpyrrolidin-3-ylamine (3.04 g), potassium carbonate (3.68 g) and dimethyl sulfoxide (20 ml) was heated at 130° C. for 7 hours. After cooling, the mixture was diluted with water and extracted with methyl tert-butyl ether. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The product with the molecular weight of 262.35 (C15H22N2O2) was obtained in this way; MS (ESI): 263 (M+H+).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methyl tert-butyl ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product with the molecular weight of 262.35 (C15H22N2O2) was obtained in this way

Sources & evidence

ORD record
ord-aa0261af899647a399602288366ed17f
Source dataset
uspto-grants-2012_10
Patent number
US08299104B2

Reaction notes

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