Triethylamine → HCID 66731937, compound

HRID 1963280Notes

Reaction equation

HRID 1963280 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16]C)=[O:15])[CH2:11][CH2:10][N:9]2[C:18]([O:20][CH3:21])=[O:19])=[CH:5][CH:4]=1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH3:21][O:20][C:18]([N:9]1[CH2:10][CH2:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][CH:8]1[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:25])([F:24])[F:1])=[CH:23][CH:22]=1)=[O:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734649HCID 66734649, compound

Product 1

HCID 66731937HCID 66731937, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(4-(trifluoromethyl)benzyl)piperidine-1,4-dicarboxylate (10.9 g, 30.33 mmol) was dissolved in acetonitrile (80 mL) and water (1.6 mL), then lithium bromide (21.07 g, 242.67 mmol) and triethylamine (16.82 mL, 121.33 mmol) were added and the resulting yellow suspension was heated at reflux. 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 Na2SO4, filtered through celite and the solvent evaporated to yield 1-(methoxycarbonyl)-2-(4-(trifluoromethyl)benzyl)piperidine-4-carboxylic acid (9.14 g, 87%).

Workup

  1. temperaturethe resulting yellow suspension was heated
  2. temperatureat reflux
  3. extractionThe organic phase was extracted with water (×2)
  4. additionTo the pooled aqueous layer was added MTBE
  5. extractionextracted with MTBE (×2)
  6. filtrationfiltered through celite
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-cca35b37da494dfa9dd77102a4cd71b2
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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