Methyl chloroformate → HCID 66734932, compound

HRID 1963135Notes

Reaction equation

HRID 1963135 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][N:9]2[C:28]([O:30][CH3:31])=[O:29])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732167HCID 66732167, compound

Product 1

HCID 66734932HCID 66734932, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-fluorophenyl)piperidine-4-carboxylate (7.4 g, 31.19 mmol) was dissolved in DCM (100 mL) and DIPEA (6.52 mL, 37.43 mmol) added followed by methyl chloroformate (2.95 mL, 37.43 mmol) at 0° C. The solution was stirred at room temperature for 1 h. The reaction mixture washed with 0.1 M HCl and satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield dimethyl 2-(4-fluorophenyl)piperidine-1,4-dicarboxylate (8.07 g, 97%) as a brown oil. MS m/z 296 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-b171a60612eb42a9a48c341fef2834a2
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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