Potassium Carbonate → HCID 71523678, compound

HRID 2178531Notes

Reaction equation

CS([O:5][CH:6]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]2=[O:25])[CH2:7]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].O[C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=1>C(#N)C>[O:25]=[C:20]1[CH2:21][CH2:22][CH2:23][CH2:24][N:19]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][N:8]1[CH2:9][CH2:10][CH:6]([O:5][C:33]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=2)[CH2:7]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl methanesulfonate a10-2 (0.183 g, 0.5 mmol, 1 eq) in acetonitrile (4 ml) is added K2CO3 (0.138 g, 1 mmol, 2 eq) and 4-hydroxybenzonitrile (0.060 g, 0.5 mmol, 1 eq). The solution is stirred overnight at 85° C. After filtration and solvent removal, the residue is purified by basic reverse phase chromatography on silicagel (gradient: CH3CN/H2O/NH4OH from 40/60/0.1 to 70/30/0.1) to give 85 mg of pure 4-[(1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)oxy]benzonitrile 50.

Workup

filtrationAfter filtration and solvent removal
customthe residue is purified by basic reverse phase chromatography on silicagel (gradient: CH3CN/H2O/NH4OH from 40/60/0.1 to 70/30/0.1)

Sources & evidence

ORD record: ord-e9ee4333aa7647d692c513e56dacdd27
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067930B2

Reaction notes

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