Methyl iodide → HCID 20095410, compound

HRID 1770100Notes

Reaction equation

HRID 1770100 reaction equation
[CH:1](NC(C)C)(C)C.[Li]CCCC.[CH2:13]([O:15][C:16]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])[CH3:14].CI>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1([CH3:1])[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])[CH3:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 20095411Ethyl 1-benzoyl-2-piperidinecarboxylateHCID 178418339Butyllithium

Product 1

HCID 20095410HCID 20095410, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diisopropyl amine (2.11 g, 25.86 mmol) in THF (50 mL) at 0° C. was added nBuLi (9.4 mL, 23.51 mmol, 2.5M in hexanes). This solution was stirred for 15 min at 0° C. and then cooled to -78° C. Ethyl-1-benzoyl-piperidine-2-carboxylate (6.16 g, 23.5 mmol) was added and the reaction was allowed to stir for 45 min at which time methyl iodide (3.34 g, 23.51 mmol) was added. The reaction was warmed to room temperature and gently warmed (~40° C.) for 2 h. The reaction was quenched with NaHCO3, extracted with ether, dried over Na2SO4 and concentrated to give ethyl-1-benzoyl-2-methyl-piperidine-2-carboxylate (6.49 g, 100% yield). 1H NMR (300 MHz, CDCl3) δ1.10 (m, 3H), 1.45 (s, 3H), 1.4-1.7 (comp m, 4H), 2.90 (m, 2H), 3.5 (m, 2H), 4.14 (m, 2H), 7.24 (m, 5H).

Workup

  1. temperaturecooled to -78° C
  2. additionwas added
  3. temperatureThe reaction was warmed to room temperature
  4. temperaturegently warmed (~40° C.) for 2 h
  5. customThe reaction was quenched with NaHCO3
  6. extractionextracted with ether
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7301a8d507ef40b59be44ab75bd01360
Source dataset
uspto-grants-1995_01
Patent number
US05385908

Reaction notes

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