Diethyl Ether → HCID 66734588, compound

HRID 1963285Notes

Reaction equation

HRID 1963285 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][CH:7]1[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][NH:8]1.CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:34])[O:32][CH3:33].CCOCC>ClCCl>[F:21][C:2]([F:20])([F:1])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][CH:7]1[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][N:8]1[C:31]([O:32][CH3:33])=[O:34]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731790Methyl 2-(3-(trifluoromethyl)benzyl)piperidine-4-carboxylate

Product 1

HCID 66734588HCID 66734588, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3-(trifluoromethyl)benzyl)piperidine-4-carboxylate (6.0 g, 19.91 mmol) was dissolved in DIPEA (6.94 mL, 39.83 mmol) and dichloromethane (150 mL). Methyl carbonochloridate (2.258 g, 23.90 mmol) was added dropwise. Ether was added and the reaction mixture was washed with 1 M HCl and Na2CO3 (aq). The organic layer was dried over MgSO4, filtered through celite and the solvent was evaporated to yield dimethyl 2-(3-(trifluoromethyl)benzyl)piperidine-1,4-dicarboxylate (6.1 g, 85%).

Workup

  1. washthe reaction mixture was washed with 1 M HCl and Na2CO3 (aq)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered through celite
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6e9493155ece485ebfe631d0c12b84e9
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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