Triethylamine → HCID 66731620, compound

HRID 1963226Notes

Reaction equation

HRID 1963226 reaction equation
[F: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>[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][CH:16]([C:18]([OH:20])=[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:10])([F:9])[F:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734680HCID 66734680, compound

Product 1

HCID 66731620HCID 66731620, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate (3.2 g, 8.81 mmol) was dissolved in acetonitrile (40 mL) and water (0.800 mL), then lithium bromide (6.12 g, 70.46 mmol) was added. Triethylamine (4.88 mL, 35.23 mmol) was added and the resulting solution was heated under reflux for 5 h. MTBE (110 mL) and water (60 mL) were added, the phases separated and the organic layer was extracted with water. The combined aqueous layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE. The combined organic layers were dried with Na2SO4 and evaporated to yield 2-(3-fluoro-4-(trifluoromethyl)phenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (3.07 g, quant.). MS m/z 348 (M−H)−

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 5 h
  3. customthe phases separated
  4. extractionthe organic layer was extracted with water
  5. extractionextracted with MTBE
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-da80a6f42eda4bc2af2bcc8770341ffa
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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