Sodium cyclopentanolate → (2-Cyclopentyloxy-6-ethoxy-3-methanesulfonyl-phenyl)-[4-(4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone

HRID 1820771Notes

Reaction equation

HRID 1820771 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])=[C:8](F)[C:7]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:6][CH:5]=1)[CH3:2].[CH:33]1([O-:38])[CH2:37][CH2:36][CH2:35][CH2:34]1.[Na+]>>[CH:33]1([O:38][C:8]2[C:7]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:6][CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]=2[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:22][CH:23]=3)[CH2:16][CH2:17]2)=[O:11])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 23691861Sodium cyclopentanolateHCID 69039060(6-Ethoxy-2-fluoro-3-methanesulfonyl-phenyl)-[4-(4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 69040251(2-Cyclopentyloxy-6-ethoxy-3-methanesulfonyl-phenyl)-[4-(4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone

Conditions

Temperature
80 °C

Procedure

0.12 mmol of (6-Ethoxy-2-fluoro-3-methanesulfonyl-phenyl)-[4-(4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone (example 55) was added to a solution of sodium cyclopentanolate (prepared from 1 mmol sodium dissolved in 1 ml of cyclopentanol). The mixture was heated for 1 hour at 80° C., poured on ice/water and extracted with ethyl acetate. Chromatography (SiO2; ethyl acetate) yielded the title compound as a slightly yellow solid. MS (m/e): 551.1 (MH+, 29%)

Workup

  1. additionpoured on ice/water
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-d4eb54fb6b5d4262974d2dd755035f68
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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