Methyl chloroformate → HCID 66734519, compound

HRID 1963182Notes

Reaction equation

HRID 1963182 reaction equation
Cl.[Cl:2][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][C:4]=1[F:19].CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[Cl:2][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][N:10]2[C:29]([O:30][CH3:31])=[O:32])=[CH:5][C:4]=1[F:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732599HCID 66732599, compound

Product 1

HCID 66734519HCID 66734519, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(4-chloro-3-fluorophenyl)piperidine-4-carboxylate hydrochloride (1.639 g, 5.32 mmol) and DIPEA (2.316 mL, 13.30 mmol) were dissolved in DCM (10 mL). Methyl carbonochloridate (0.503 mL, 6.38 mmol) was added dropwise and the reaction stirred at room temperature for 2 h. The reaction mixture was diluted with DCM (100 mL) and washed with 0.1 M HCl (2×75 mL), sat. NaHCO3 (100 mL), dried through a phase separator and evaporated in vacuo yielding dimethyl 2-(4-chloro-3-fluorophenyl)piperidine-1,4-dicarboxylate (1.625 g, 93%) as a colorless oil. MS m/z 330 (M+H)+

Workup

  1. washwashed with 0.1 M HCl (2×75 mL), sat. NaHCO3 (100 mL)
  2. customdried through a phase separator
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-9986e11b6e974cbc93e1830ab50472d0
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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