Acetonitrile → HCID 66731973, compound

HRID 1963172Notes

Reaction equation

HRID 1963172 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH:13]([C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][N:10]1[C:19]([O:21][CH3:22])=[O:20].C(#N)C.[Br-].[Li+].CCN(CC)CC>CC(OC)(C)C.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][CH2:11][N:10]1[C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 82050Lithium BromideHCID 66734584Dimethyl 2-(2,4-difluorophenyl)piperidine-1,4-dicarboxylate

Product 1

HCID 66731973HCID 66731973, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Dimethyl 2-(2,4-difluorophenyl)piperidine-1,4-dicarboxylate (2.38 g, 7.60 mmol) was dissolved into acetonitrile (35 mL) and water (0.700 mL), then lithium bromide (5.28 g, 60.77 mmol) was added. Et3N (4.24 mL, 30.39 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 water layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE (2 times). The combined organic layer was dried over Na2SO4, filtered and evaporated yielding 2-(2,4-difluorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (2.27, quant.) as a slightly yellow semi-solid. MS m/z 300 (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. extractionextracted with MTBE (2 times)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-01197308a24b43f8b805a51b36669c8a
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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