Acetonitrile → HCID 66732298, compound

HRID 1963140Notes

Reaction equation

HRID 1963140 reaction equation
[Cl: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.C(#N)C.[Br-].[Li+].CCN(CC)CC>CC(OC)(C)C.O>[Cl: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 6342AcetonitrileHCID 8471TriethylamineHCID 82050Lithium BromideHCID 66734970HCID 66734970, compound

Product 1

HCID 66732298HCID 66732298, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Dimethyl 2-(4-chlorophenyl)piperidine-1,4-dicarboxylate (3.97 g, 12.73 mmol) was dissolved into acetonitrile (55 mL) and water (1.1 mL), then lithium bromide (8.85 g, 101.87 mmol) was added. Et3N (7.10 mL, 50.94 mmol) was added and the resulting yellow suspension was heated at reflux for 2 h. Water (100 mL) and MTBE (150 mL) were added. The phases were separated and the organic layer was extracted with water (2×). The pooled water layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE (2×). The combined organic layer was dried over Na2SO4, filtered and evaporated leaving 2-(4-chlorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (3.49 g, 92%) as a yellow semi-solid. MS m/z 298 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-3c93228ddadb44f5b1764fbdccedd1c6
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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