Triethylamine → HCID 66732502, compound

HRID 1963230Notes

Reaction equation

HRID 1963230 reaction equation
[C:1]1([CH:7]2[CH2:12][CH:11]([C:13]([O:15]C)=[O:14])[CH2:10][CH2:9][N:8]2[C:17]([O:19][CH3:20])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH3:20][O:19][C:17]([N:8]1[CH2:9][CH2:10][CH:11]([C:13]([OH:15])=[O:14])[CH2:12][CH:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66732437HCID 66732437, compound

Product 1

HCID 66732502HCID 66732502, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-phenylpiperidine-1,4-dicarboxylate (5.88 g, 21.20 mmol) was dissolved in acetonitrile (60 mL) and water (1.2 mL), then lithium bromide (4.25 mL, 169.63 mmol) was added. Triethylamine (11.76 mL, 84.81 mmol) was added and the resulting yellow suspension was heated at reflux for 1 h. Water (60 mL) and MTBE were added. The organic phase was extracted with water (×2). To the pooled aqueous layer was added MTBE and the solution was acidified to pH 1 with 3.8 M aq HCl and then extracted with MTBE (×2). The combined organic layer was washed with water and evaporated. Traces of water were azeotropically removed by MeCN. 1-(Methoxycarbonyl)-2-phenylpiperidine-4-carboxylic acid (5.25 g, 94%) was isolated as a slightly yellow semisolid. MS m/z 264 (M+H)+

Workup

  1. temperaturethe resulting yellow suspension was heated
  2. temperatureat reflux for 1 h
  3. extractionThe organic phase was extracted with water (×2)
  4. additionTo the pooled aqueous layer was added MTBE
  5. extractionextracted with MTBE (×2)
  6. washThe combined organic layer was washed with water
  7. customevaporated
  8. customTraces of water were azeotropically removed by MeCN

Sources & evidence

ORD record
ord-f2442854837c48239bbd174926d25c9b
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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