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

HRID 661200
Notes
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Reaction equation

HRID 661200 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[F:14][C:15]([F:34])([F:33])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][NH:27][CH2:26][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[F:34][C:15]([F:14])([F:33])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][N:27]([C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[CH2:26][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:24]2)=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58002737Methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate

Product 1

HCID 580025493-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethoxy)phenyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 5.32 g (26.4 mmol) of 4-nitrophenyl chloroformate were added slowly to 8.0 g (26.4 mmol) of methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate and 5.34 g (26.3 mmol) of triethylamine in 666 ml of dichloromethane. The mixture was stirred at RT for 2 h. For workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution, then with water. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2->1:1). Yield: 7.32 g (54% of theory)

Workup

  1. washFor workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2->1:1)

Sources & evidence

ORD record
ord-fa4e461019b44a24b11f69a92aa2baba
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084469B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes