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Methyl chloroformate → Dimethyl 2-(4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate

HRID 1963147
Notes
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Reaction equation

HRID 1963147 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:30](Cl)(=[O:33])[O:31][CH3:32]>C(Cl)Cl>[F:20][C:2]([F:19])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]2[C:30]([O:31][CH3:32])=[O:33])=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 667318002-(4-Trifluoromethyl-phenyl)-piperidine-4-carboxylic acid methyl ester

Product 1

HCID 66734728Dimethyl 2-(4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylateYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

Methyl 2-(4-(trifluoromethyl)phenyl)piperidine-4-carboxylate (4.973 g, 17.31 mmol) was dissolved in DCM (100 mL) and DIPEA (3.62 mL, 20.77 mmol) added followed by methyl carbonochloridate (1.636 mL, 20.77 mmol). The solution was stirred at room temperature for 1 h 45 min. The reaction mixture was washed with 0.1 M HCl and satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield crude dimethyl 2-(4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate (6.05 g, 101%) as a brown oil. MS m/z 346 (M+H)+

Workup

  1. washThe reaction mixture was washed with 0.1 M HCl
  2. customevaporated

Sources & evidence

ORD record
ord-ef086c98d9154fe091ab841360477f90
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415378B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes