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

HRID 2091744Notes

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 methyl 5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylate (Example 13A) were dissolved in 1.0 l of dichloromethane, and admixed at 0° C. with 14.1 g (139 mmol) of triethylamine Subsequently, 14.0 g (69.6 mmol) of 4-nitrophenyl chlorocarbonate were 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 hydrogencarbonate 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 hydrogencarbonate 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-df2483d00bfc43e08c14826da530e556
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440657B2

Reaction notes

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