Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethyl)phenyl]piperidine-1,3-dicarboxylate

HRID 876253Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:39])[O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1>ClCCl>[F:20][C:2]([F:19])([F:1])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:28]([O:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:39])[CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

20.0 g (69.6 mmol) of the compound from Example 53A were dissolved in 1.0 l of dichloromethane, and 14.1 g (139 mmol) of triethylamine were added at 0° C. 14.0 g (69.6 mmol) of 4-nitrophenyl chlorocarbonate were then added dropwise. The reaction mixture was stirred at 0° C. for 2 h and then at RT for 16 h. For workup, the mixture was washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. This gave 31.3 g of crude product, which was reacted without any further purification steps.

Workup

waitat RT for 16 h
washFor workup, the mixture was washed with saturated aqueous sodium bicarbonate solution
dry with materialThe organic phase was dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThis gave 31.3 g of crude product, which was reacted without any further purification steps

Sources & evidence

ORD record: ord-1257b7c5762c46bd9a1c0c19d14b6878
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987248B2

Reaction notes

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