Methyl iodide → HCID 18997143, compound

HRID 1708049Notes

Reaction equation

HRID 1708049 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[C:13]1([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.IC>C1COCC1>[C:13]1([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][C:24]([CH3:1])([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 18997131HCID 18997131, compoundHCID 178418339Butyllithium

Product 1

HCID 18997143HCID 18997143, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 2.64 mL (18.9 mmol) of diisopropylamine in 30 mL of dry THF at -78° was added 6.9 mL (17.3 mmol) of 2.5M n-butyllithium in hexanes. The mixture was allowed to warm to room temperature and then was cooled once again to -78°. To the stirred solution was added 4.11 g (15.7 mmol) of 1-(2-phenylethyl)-4-carboethoxypiperidine in 25 mL of dry THF. The mixture was allowed to warm to -40° and 0.98 mL (15.7 mmol) of iodomethane was added to the reaction mixture. The mixture was stirred at -40° for 15 minutes and then allowed to stir at room temperature for 3 hours. The mixture was evaporated to dryness and the residue was dissolved in water. The aqueous solution was extracted with methylene chloride and the extracts were dried and evaporated to give 3.70 g of 1-(2-phenylethyl)-4-methyl-4-carboethoxypiperidine as a yellow oil. NMR (CDCl3) δ7.15-7.21 (m, 5H); 4.11-4.20 (q, 4H); 2.71-2.94 (m, 4H): 2.52-2.61 (m, 2H): 2.11-2.24 (m, 4H); 1.47-1.59 (m, 2H); 1.21-1.30 (t, 3H); 1.20 (s, 3H).

Workup

  1. temperaturewas cooled once again to -78°
  2. temperatureto warm to -40°
  3. stirringto stir at room temperature for 3 hours
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe residue was dissolved in water
  6. extractionThe aqueous solution was extracted with methylene chloride
  7. customthe extracts were dried
  8. customevaporated

Sources & evidence

ORD record
ord-112c55d4e8854576bfff811abf2a9951
Source dataset
uspto-grants-1994_10
Patent number
US05356906

Reaction notes

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