Water → HCID 22494735, compound

HRID 1816704Notes

Reaction equation

CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:26][CH:27]1[O:32][CH:31]([CH3:33])[CH2:30][NH:29][CH2:28]1.O>CN(C)C=O>[CH3:33][CH:31]1[O:32][CH:27]([CH3:26])[CH2:28][N:29]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:30]1

Participants

Conditions

Temperature: 92.5 °C

Procedure

To a solution of 4-(4-methanesulfonyloxypiperidin-1-yl)benzonitrile (4.90 g) in N,N-dimethylformamide (DMF) (50 ml) were added potassium carbonate (4.83 g) and 2,6-dimethylmorpholine (3.02 g), and the mixture was stirred at 90-95° C. for 6 hours. After cooling, the reaction mixture was poured into water (300 ml) and extracted twice with a mixture of ethyl acetate and n-hexane (100 ml:30 ml). The extracts were combined and washed in turn with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting precipitates were washed with IPE (100 ml), collected by filtration and dried in vacuo to give 4-[4-(2,6-dimethylmorpholin-4-yl)piperidin-1-yl]benzonitrile (2.29 g).

Workup

temperatureAfter cooling
extractionextracted twice with a mixture of ethyl acetate and n-hexane (100 ml:30 ml)
washwashed in turn with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo
customThe resulting precipitates
washwere washed with IPE (100 ml)
filtrationcollected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-737f38f1d996427ca1a5771450db146d
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884868B1

Reaction notes

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