Methyl chloroformate → HCID 68503986, compound

HRID 1963190Notes

Reaction equation

HRID 1963190 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]2)[CH:6]=[C:7]([Cl:9])[CH:8]=1.CCN(C(C)C)C(C)C.Cl[C:30]([O:32][CH3:33])=[O:31]>C(Cl)Cl>[Cl:9][C:7]1[CH:6]=[C:5]([CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][N:11]2[C:30]([O:32][CH3:33])=[O:31])[CH:4]=[C:3]([Cl:2])[CH:8]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731788HCID 66731788, compound

Product 1

HCID 68503986HCID 68503986, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(3,5-dichlorophenyl)piperidine-4-carboxylate hydrochloride (4.8 g, 14.79 mmol) was dissolved in DCM (41.5 mL) and DIPEA (6.46 mL, 36.97 mmol). Methyl chloroformate (1.374 mL, 17.74 mmol) was added and the reaction mixture was stirred at room temperature for 1 h, then diluted with DCM and washed with 0.3 M HCl and brine. The organic layer was filtered through a phase separator and evaporated to give dimethyl 2-(3,5-dichlorophenyl)-piperidine-1,4-dicarboxylate (5.3 g) as an oil. MS m/z 346 (M+H)+

Workup

  1. washwashed with 0.3 M HCl and brine
  2. filtrationThe organic layer was filtered through a phase separator
  3. customevaporated

Sources & evidence

ORD record
ord-e7968859a6b64a9aa9a25cf104bb5e4a
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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