Triethylamine → HCID 66731655, compound

HRID 1963195Notes

Reaction equation

HRID 1963195 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[CH:13]1[CH2:18][CH:17]([C:19]([O:21]C)=[O:20])[CH2:16][CH2:15][N:14]1[C:23]([O:25][CH3:26])=[O:24].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[CH:13]1[CH2:18][CH:17]([C:19]([OH:21])=[O:20])[CH2:16][CH2:15][N:14]1[C:23]([O:25][CH3:26])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734961Dimethyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)piperidine-1,4-dicarboxylate

Product 1

HCID 66731655HCID 66731655, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(2-fluoro-4-(trifluoromethoxy)phenyl)piperidine-1,4-dicarboxylate (5.35 g, 14.10 mmol) was dissolved in acetonitrile (100 mL) and water (2.000 mL), then lithium bromide (9.80 g, 112.84 mmol) was added. Triethylamine (7.82 mL, 56.42 mmol) was added and the resulting suspension was heated under reflux for 7 h. MTBE (350 mL) and water (180 mL) were added, the phases separated and the organic layer was extracted with water. The combined aqueous layers were acidified with 3.8 M HCl and extracted with EtOAc. The combined organic layers were dried with Na2SO4 and evaporated. 2-(2-Fluoro-4-(trifluoromethoxy)phenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (5.09 g, 99%) was yielded as a colorless solid. MS m/z 364 (M−H)−

Workup

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

Sources & evidence

ORD record
ord-c2551da773344ad2b2b50f9b831e0e24
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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