Methyl chloroformate → HCID 66734712, compound

HRID 1963143Notes

Reaction equation

HRID 1963143 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:7][CH:8]=1.CCN(C(C)C)C(C)C.Cl[C:31]([O:33][CH3:34])=[O:32]>C(Cl)Cl>[F:20][C:2]([F:19])([F:1])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]2[C:31]([O:33][CH3:34])=[O:32])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731779HCID 66731779, compound

Product 1

HCID 66734712HCID 66734712, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3-(trifluoromethyl)phenyl)piperidine-4-carboxylate (1.4 g, 4.87 mmol) was dissolved in DCM (50 mL), then DIPEA (2.128 mL, 12.18 mmol) was added. Methyl chloroformate (0.537 mL, 6.82 mmol) was added dropwise to the solution. The reaction mixture was stirred at room temperature for 4 h, washed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL), dried through a phase separator and evaporated yielding dimethyl 2-(3-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate (1.7 g, quant.) as an orange oil. MS m/z 346 (M+H)+

Workup

  1. washwashed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL)
  2. customdried through a phase separator
  3. customevaporated

Sources & evidence

ORD record
ord-be91eb661e8e44af8d40622c3ef93e16
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

Loading…