Methyl N-(triethylammoniosulfonyl)carbamate → 1-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carbonitrile

HRID 1642824Notes

Reaction equation

CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[N:16]1([C:22]([N:24]2[CH2:29][CH:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)[CH2:27][CH:26]([C:40]([NH2:42])=O)[CH2:25]2)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>O1CCCC1>[N:16]1([C:22]([N:24]2[CH2:29][CH:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:32][CH:31]=3)[CH2:27][CH:26]([C:40]#[N:42])[CH2:25]2)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 70 °C

Procedure

Under argon, 3.83 g (16.1 mmol) of Burgess reagent were added to a solution of 4.42 g (11.5 mmol) of the compound from Example 82A in 208 ml of tetrahydrofuran. The mixture was stirred at 70° C. for 1 h. For work-up, the solvent was removed under reduced pressure and the residue was taken up in ethyl acetate. The organic phase was washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. Yield: 4.19 g (99% of theory)

Workup

customFor work-up, the solvent was removed under reduced pressure
washThe organic phase was washed successively with water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-50799a67b6e0458f9b92f3610d463aa0
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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