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Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-1,3-dicarboxylate

HRID 2091768
Notes
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Reaction equation

HRID 2091768 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:31]>ClCCl>[F:21][C:2]([F:1])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][N:14]([C:30]([O:32][C:33]3[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=3)=[O:31])[CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116537Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

Product 1

HCID 581164903-Methyl 1-(4-nitrophenyl) 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

A solution of 6.62 g (19.8 mmol, purity 90%) of the compound from Example 42A in dichloromethane (211 ml) was admixed with 9.65 ml (7.00 g, 69.2 mmol) of triethylamine and then admixed at 0° C. with 3.99 g (19.8 mmol) of 4-nitrophenyl chloroformate. The mixture was warmed to RT and stirred for 1 h. The reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 10.3 g (91% of theory, purity 81%)

Workup

  1. washThe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f58416ad8f54a348b03e9a3c907068d
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440657B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes