Methyl chloroformate → Dimethyl 2-(2-methyl-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate

HRID 1963217Notes

Reaction equation

HRID 1963217 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[CH:13]1[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15][NH:14]1.CCN(C(C)C)C(C)C.[C:32](Cl)(=[O:35])[O:33][CH3:34]>ClCCl>[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:4]=1[CH:13]1[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15][N:14]1[C:32]([O:33][CH3:34])=[O:35]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732222Methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate hydrochloride

Product 1

HCID 66734452Dimethyl 2-(2-methyl-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylateYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate hydrochloride (8.2 g, 24.28 mmol) and DIPEA (10.60 mL, 60.69 mmol) were dissolved in dichloromethane (100 mL). Methyl carbonochloridate (2.257 mL, 29.13 mmol) was added and the reaction stirred at room temperature for 1 h. DCM (100 mL) was added. The organic phase was washed twice with 1 M HCl and water, dried over Na2SO4 and evaporated to yield dimethyl 2-(2-methyl-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate (8.9 g, quant.). MS m/z 360 (M+H)+

Workup

  1. washThe organic phase was washed twice with 1 M HCl and water
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-606d8e10c1d54e168691d6fd94314280
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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