Methyl chloroformate → HCID 66734970, compound

HRID 1963139Notes

Reaction equation

HRID 1963139 reaction equation
[Cl: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.[C:27](Cl)(=[O:30])[O:28][CH3:29]>C(Cl)Cl>[Cl: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:27]([O:28][CH3:29])=[O:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732206HCID 66732206, compound

Product 1

HCID 66734970HCID 66734970, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-chlorophenyl)piperidine-4-carboxylate (3.13 g, 12.34 mmol) was dissolved in DCM (50 mL), then DIPEA (5.39 mL, 30.84 mmol) was added. Methyl carbonochloridate (1.360 mL, 17.27 mmol) was added dropwise to the solution. The mixture was stirred at room temperature for 3 h. The mixture was washed with 0.1 M HCl (2*100 mL) and satd NaHCO3 (100 mL), then dried through a phase-separator and evaporated yielding dimethyl 2-(4-chlorophenyl)piperidine-1,4-dicarboxylate (3.97 g, quant.) as an orange oil. MS m/z 312 (M+H)+

Workup

  1. washThe mixture was washed with 0.1 M HCl (2*100 mL) and satd NaHCO3 (100 mL)
  2. customdried through a phase-separator
  3. customevaporated

Sources & evidence

ORD record
ord-277bc6cd5e86401fa7bfec4b9d2607f2
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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