Triethylamine → HCID 66732169, compound

HRID 1963338Notes

Reaction equation

HRID 1963338 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([F:24])[C:22]=1[F:23])[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:3]=[C:2]([F:1])[C:22]([F:23])=[C:21]([F:24])[CH:20]=1)=[O:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734590HCID 66734590, compound

Product 1

HCID 66732169HCID 66732169, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(3,4,5-trifluorobenzyl)piperidine-1,4-dicarboxylate (4.01 g, 11.61 mmol) was dissolved in acetonitrile (40 mL) and water (0.8 mL). Lithium bromide (2.329 mL, 92.90 mmol) was added followed by triethylamine (6.44 mL, 46.45 mmol). The reaction was refluxed for 2 h. The reaction was cooled to room temperature. Water (200 mL) and MTBE (150 mL) were added, shaken and the phases separated. The organic phase was extracted with water (2×150 mL). The combined aqueous phases were acidified with 3 M HCl to pH 1 and then extracted with MTBE (2×400 mL). The combined organic phases were dried with Na2SO4, filtered and evaporated in vacuo to yield 1-(methoxycarbonyl)-2-(3,4,5-trifluoro-benzyl)piperidine-4-carboxylic acid (3.42 g, 89%) as a light brown foam. MS m/z 330 (M−H)−

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. customthe phases separated
  3. extractionThe organic phase was extracted with water (2×150 mL)
  4. extractionextracted with MTBE (2×400 mL)
  5. dry with materialThe combined organic phases were dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-5565a10f0b354b40ad5969a5c635e8e8
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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