Water → 4-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile

HRID 657513Notes

Reaction equation

HRID 657513 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:22])[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH:26]1[CH2:28][CH2:27]1.[H-].[Na+].O>CN(C=O)C>[CH:26]1([CH2:25][CH2:24][O:22][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][C:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 22636989(2-Bromoethyl)cyclopropane2×HCID 594425734-(4-Fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

Product 1

HCID 594425114-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrileYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg of the compound of Example 1, 760 mg of (2-bromoethyl)cyclopropane (Chorvat et al., J. Med. Chem. 28, 194-200 (1985)) and 122 mg of sodium hydride in 20 ml of anhydrous DMF were stirred at room temperature for 19 h. 760 mg of (2-bromoethyl)cyclopropane and 122 mg of sodium hydride were then added and the mixture was stirred at room temperature for 4 days. The reaction mixture was then treated with 100 ml of water and extracted three times with 50 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 290 mg of the title compound were obtained as a pale yellow oil.

Workup

  1. extractionextracted three times with 50 ml each of EA
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f6ffb8353fe14f5891972cf2c9430c43
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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