Triethylamine → HCID 66731694, compound

HRID 1963160Notes

Reaction equation

HRID 1963160 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH:15]([C:17]([O:19]C)=[O:18])[CH2:14][CH2:13][N:12]2[C:21]([O:23][CH3:24])=[O:22])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH3:24][O:23][C:21]([N:12]1[CH2:13][CH2:14][CH:15]([C:17]([OH:19])=[O:18])[CH2:16][CH:11]1[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=1)=[O:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734661HCID 66734661, compound

Product 1

HCID 66731694HCID 66731694, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(4-(methylsulfonyl)phenyl)piperidine-1,4-dicarboxylate (5.952 g, 16.75 mmol) was dissolved in acetonitrile (50 mL) and water (1.000 mL), then lithium bromide (11.64 g, 133.98 mmol) added. Triethylamine (9.29 mL, 66.99 mmol) was added and the reaction mixture heated under reflux for 1.5 h. MTBE (150 mL) and water (150 mL) were added, shaken and the phases separated. The organic phase was extracted with water (2×200 mL). The combined aqueous phases were acidified to pH 1 with 3 M HCl and extracted with MTBE (2×500 mL). The combined organic phases were dried with Na2SO4, filtered and evaporated in vacuo yielding 1-(methoxycarbonyl)-2-(4-(methylsulfonyl)phenyl)piperidine-4-carboxylic acid (4.76 g, 83%). MS m/z 342 (M+H)+

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 1.5 h
  3. customthe phases separated
  4. extractionThe organic phase was extracted with water (2×200 mL)
  5. extractionextracted with MTBE (2×500 mL)
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-ff5da0ac01aa49f68a3b2f131fc79a97
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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