Methyl chloroformate → HCID 66734975, compound

HRID 1963186Notes

Reaction equation

HRID 1963186 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl: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>[Cl:2][C:3]1[CH:8]=[C:7]([Cl: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 66731744HCID 66731744, compound

Product 1

HCID 66734975HCID 66734975, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(2,4-dichlorophenyl)piperidine-4-carboxylate hydrochloride (2.8 g, 8.63 mmol) was diluted with DCM (24.18 mL). DIPEA (3.76 mL, 21.56 mmol) and methyl carbonochloridate (0.815 mL, 10.35 mmol) were added. The reaction mixture was stirred at room temperature for 30 min, then washed with 3×0.1 M HCl and brine. Filtered through a phase separator. Evaporated to yield dimethyl 2-(2,4-dichlorophenyl)piperidine-1,4-dicarboxylate (2.78 g, 93%) as an oil. MS m/z 346 (M+H)+

Workup

  1. washwashed with 3×0.1 M HCl and brine
  2. filtrationFiltered through a phase separator
  3. customEvaporated

Sources & evidence

ORD record
ord-ebdc1f6d00a249b98723548bbe4ddc7e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…