Water → 2-(4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)-4-cyanopiperidin-1-yl)acetic Acid Ethyl Ester

HRID 31113Notes

Reaction equation

HRID 31113 reaction equation
Cl.[CH:2]1([O:7][C:8]2[CH:9]=[C:10]([C:18]3([C:24]#[N:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O>CN(C)C=O>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][N:21]1[CH2:20][CH2:19][C:18]([C:10]2[CH:11]=[CH:12][C:13]([O:14][CH:15]([F:17])[F:16])=[C:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:9]=2)([C:24]#[N:25])[CH2:23][CH2:22]1)[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 23034797HCID 23034797, compound

Product 1

HCID 102737732-(4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)-4-cyanopiperidin-1-yl)acetic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound prepared in example 1 (19.8 g) in N,N-dimethylformamide (53 ml) were added potassium carbonate (18.4 g) and ethyl bromoacetate (5.89 ml) and the mixture was stirred for 1.5 hours at 50° C. To the reaction mixture was added water (160 ml) and it was extracted by tert-butyl methyl ether (160 ml). The organic layer was washed by water (80 ml×2) and concentrated to give the title compound (23.4 g) having the following physical data.

Workup

  1. extractionwas extracted by tert-butyl methyl ether (160 ml)
  2. washThe organic layer was washed by water (80 ml×2)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f98b3023b5b94e2ca249606c500046de
Source dataset
uspto-grants-2008_09
Patent number
US07425567B2

Reaction notes

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