Triethylamine → HCID 66732276, compound

HRID 1963136Notes

Reaction equation

HRID 1963136 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH:12]([C:14]([O:16]C)=[O:15])[CH2:11][CH2:10][N:9]2[C:18]([O:20][CH3:21])=[O:19])=[CH:4][CH:3]=1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH2:11][CH2:10][N:9]2[C:18]([O:20][CH3:21])=[O:19])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734932HCID 66734932, compound

Product 1

HCID 66732276HCID 66732276, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(4-fluorophenyl)piperidine-1,4-dicarboxylate (8.97 g, 30.38 mmol) was dissolved in acetonitrile (60 mL) and water (1.200 mL), then lithium bromide (21.10 g, 243.00 mmol) was added. Triethylamine (16.84 mL, 121.50 mmol) was added and the resulting brown suspension was heated under reflux for 1 h. Water (120 mL) and MTBE (120 mL) were added. The organic phase was extracted with water (2×25 mL). The pooled aqueous layer was acidified to pH 1 with 6 M HCl and extracted with MTBE (2×150 mL). The combined organic layer was washed with water (25 mL), dried over anhydrous Na2SO4 and evaporated. 2-(4-Fluorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (8.4 g, 98%) was isolated as a brown oil.

Workup

  1. temperaturethe resulting brown suspension was heated
  2. temperatureunder reflux for 1 h
  3. extractionThe organic phase was extracted with water (2×25 mL)
  4. extractionextracted with MTBE (2×150 mL)
  5. washThe combined organic layer was washed with water (25 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-c2c1336076e6442ea0233f40000cc1a8
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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