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

HRID 1963171Notes

Reaction equation

HRID 1963171 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][N:11]1[C:29]([O:30][CH3:31])=[O:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731925Methyl 2-(2,4-difluorophenyl)piperidine-4-carboxylate hydrochloride

Product 1

HCID 66734584Dimethyl 2-(2,4-difluorophenyl)piperidine-1,4-dicarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(2,4-difluorophenyl)piperidine-4-carboxylate hydrochloride (2.34 g, 8.02 mmol) was dissolved in DCM (50 mL), then DIPEA (3.50 mL, 20.05 mmol) was added. Methyl carbonochloridate (0.884 mL, 11.23 mmol) was added dropwise to the solution. The mixture was stirred at room temperature for 4 h, washed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL), then dried through a phase-separator and evaporated yielding dimethyl 2-(2,4-difluorophenyl)piperidine-1,4-dicarboxylate (2.38 g, 95%) as an orange oil.

Workup

  1. washwashed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL)
  2. customdried through a phase-separator
  3. customevaporated

Sources & evidence

ORD record
ord-64288e0017a94c4980df06aa7cc1d94f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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