Water → HCID 68864364, compound

HRID 229117Notes

Reaction equation

HRID 229117 reaction equation
[C:1]1([CH:7]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:12]=2[Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][C:28]#N.[C:30]([O-:33])([O-])=[O:31].[K+].[K+].[OH2:36]>>[C:1]1([CH:7]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:8][N:9]([CH2:8][CH2:7][CH2:22][O:36][C:6]2[CH2:5][C:28](=[CH:27][C:30]([OH:33])=[O:31])[CH:3]=[CH:2][CH:1]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[C:12]=2[Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 68863219HCID 68863219, compound

Product 1

HCID 68864364HCID 68864364, compoundYield 50%

Procedure

A solution of N-(2-Phenyl-2-cyclopentylethyl)-2-chloro-3-trifluoromethylbenzylamine (218 mg, 0.57 mmol), methyl 3-(3-iodopropyloxy)-phenyl acetate (181 mg, 0.54 mmol), and MeCN (6 mL) was treated with K2CO3 (75 mg, 0.54 mmol), and the mixture was refluxed for 12 h. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent evaporated. The residue was purified via silica gel column chromatography eluted with 10% EtOAc:hexane to give the titled compound (159 mg, 50%). MS (ESI) 588 (M+H+).

Workup

  1. temperaturethe mixture was refluxed for 12 h
  2. extractionextracted with Et2O
  3. washThe extracts were washed with H2O
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was purified via silica gel column chromatography
  7. washeluted with 10% EtOAc

Sources & evidence

ORD record
ord-f41aa00c735f43ed8780e19a82182b7f
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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