Triethylamine → HCID 66731649, compound

HRID 1963199Notes

Reaction equation

HRID 1963199 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][CH:14]([C:16]([O:18]C)=[O:17])[CH2:13][CH2:12][N:11]2[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[Br-].[Li+].CCN(CC)CC.CC(OC)(C)C>C(#N)C.O>[CH3:23][O:22][C:20]([N:11]1[CH2:12][CH2:13][CH:14]([C:16]([OH:18])=[O:17])[CH2:15][CH:10]1[C:4]1[CH:5]=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[CH:3]=1)=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734904HCID 66734904, compound

Product 1

HCID 66731649HCID 66731649, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(3,4,5-trifluorophenyl)piperidine-1,4-dicarboxylate (2.77 g, 8.36 mmol) was dissolved in acetonitrile (35 mL) and water (0.700 mL), then lithium bromide (5.81 g, 66.89 mmol) was added. Et3N (4.66 mL, 33.45 mmol) was added and the resulting yellow suspension was heated under reflux for 2 h. Water (50 mL) and MTBE (150 mL) were added. The phases were separated and the organic layer was extracted with water (2 times). The pooled aqueous layers were acidified to pH 1 with 3.8 M HCl and with MTBE (2 times). The combined organic layer was dried over Na2SO4, filtered and evaporated yielding 1-(methoxycarbonyl)-2-(3,4,5-trifluorophenyl)piperidine-4-carboxylic acid (2.23 g, 84%) as a slightly yellow semi-solid. MS m/z 316 (M−H)−

Workup

  1. temperaturethe resulting yellow suspension was heated
  2. temperatureunder reflux for 2 h
  3. customThe phases were separated
  4. extractionthe organic layer was extracted with water (2 times)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-24d627ae1961490fa1e1e67db637000b
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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