Triethylamine → HCID 66731806, compound

HRID 1963210Notes

Reaction equation

HRID 1963210 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][CH:16]([C:18]([O:20]C)=[O:19])[CH2:15][CH2:14][N:13]2[C:22]([O:24][CH3:25])=[O:23])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH3:25][O:24][C:22]([N:13]1[CH2:14][CH2:15][CH:16]([C:18]([OH:20])=[O:19])[CH2:17][CH:12]1[C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:9])[F:10])=[C:2]([CH3:1])[CH:3]=1)=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66735077HCID 66735077, compound

Product 1

HCID 66731806HCID 66731806, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(3-methyl-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate (3.09 g, 8.60 mmol) was dissolved in acetonitrile (30 mL) and water (0.6 mL), lithium bromide (5.97 g, 68.79 mmol) was added. Triethylamine (3.48 g, 34.40 mmol) was added and the resulting suspension was heated under reflux for 1 h. Water (60 mL) and MTBE were added. The organic phase was extracted with water (×2). To the pooled aqueous layer was added MTBE and the solution was acidified to pH 1 with HCl and then extracted with MTBE (×2). The organic layer was dried over Na2SO4, filtered through celite and the solvent evaporated to yield 1-(methoxycarbonyl)-2-(3-methyl-4-(trifluoromethyl)phenyl)piperidine-4-carboxylic acid (2.65 g, 7.67 mmol).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 1 h
  3. extractionThe organic phase was extracted with water (×2)
  4. additionTo the pooled aqueous layer was added MTBE
  5. extractionextracted with MTBE (×2)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered through celite
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-f93685f93bf74d448c5e66562c87c88c
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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