Methyl chloroformate → Dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylate

HRID 1963311Notes

Reaction equation

HRID 1963311 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH2:7][NH:6]1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH2:7][N:6]1[C:29]([O:30][CH3:31])=[O:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731652HCID 66731652, compound

Product 1

HCID 66734456Dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(2,5-difluorobenzyl)piperidine-4-carboxylate (6.65 g, 24.69 mmol) in DCM (100 mL) and DIPEA (5.16 mL, 29.63 mmol) was added methyl carbonochloridate (2.53 mL, 32.10 mmol) dropwise at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 1 h. The reaction was quenched with 0.15 M HCl (250 mL). The organic phase was separated, washed with satd NaHCO3, dried using a phase separator and evaporated to yield dimethyl 2-(2,5-difluorobenzyl)piperidine-1,4-dicarboxylate (8.1 g, 100%). MS m/z 328 (M+H)+

Workup

  1. customThe reaction was quenched with 0.15 M HCl (250 mL)
  2. customThe organic phase was separated
  3. washwashed with satd NaHCO3
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-85bee873ae75481ebb7a13eca800befe
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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