Triethylamine → HCID 66732367, compound

HRID 1963291Notes

Reaction equation

HRID 1963291 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]([O:14]C)=[O:13])[CH2:9][CH2:8][N:7]1[C:16]([O:18][CH3:19])=[O:17].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH3:19][O:18][C:16]([N:7]1[CH2:8][CH2:9][CH:10]([C:12]([OH:14])=[O:13])[CH2:11][CH:6]1[CH2:5][C:4]1[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=1[C:2]([F:25])([F:24])[F:1])=[O:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734864HCID 66734864, compound

Product 1

HCID 66732367HCID 66732367, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Crude dimethyl 2-(2-(trifluoromethyl)benzyl)piperidine-1,4-dicarboxylate (5.42 g, 15.15 mmol) was dissolved in acetonitrile (40 mL) and water (0.800 mL). lithium bromide (9.66 g, 111.20 mmol) and triethylamine (7.71 mL, 55.60 mmol) were added and the mixture was heated at reflux for 1 h 45 min. Water (90 mL) and MTBE were added. The organic phase was extracted with water. To the pooled aqueous layer was added MTBE and the solution was acidified to pH 1 with 2 M HCl and then extracted with MTBE (×2). The combined organic layer was dried over Na2SO4 and evaporated to give 1-(methoxycarbonyl)-2-(2-(trifluoromethyl)benzyl)piperidine-4-carboxylic acid (4.72 g, 98%) as a slightly yellow semisolid. MS m/z 346 (M+H)+

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h 45 min
  3. extractionThe organic phase was extracted with water
  4. additionTo the pooled aqueous layer was added MTBE
  5. extractionextracted with MTBE (×2)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-924ce0cd5e3d43db8ef2f656bae6cbe3
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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