Methyl iodide → HCID 21093753, compound

HRID 1349945Notes

Reaction equation

HRID 1349945 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:5]=2[O:4][CH2:3]1.[H-].[Na+].I[CH3:29]>CN(C)C=O>[CH3:29][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)[C:5]=2[O:4][CH2:3][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21093752HCID 21093752, compound

Product 1

HCID 21093753HCID 21093753, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of tert-butyl 4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-ylmethyl)piperidine-1-carboxylate (0.6 g, 1.73 mmol) in anhydrous N,N-dimethylformamide (1 mL), was added dropwise to a stirred suspension of sodium hydride (60%) (0.08 g) in anhydrous N,N-dimethylformamide (12 mL) at 0° C. Stirring was continued for a further 20 mins. before iodomethane (0.5 g) in anhydrous N,N-dimethylformamide (1 mL) was added. The mixture was allowed to stir at room temperature for 4 hours. It was quenched with saturated ammonium chloride (20 mL) and extracted with diethyl ether (100 mL). The organic layer was dried (Na2SO4) and evaporated in vacuo to give a crude oil. Silica gel chromatography eluting with ethyl acetate in hexane (10–20%) gave the title compound as a solid (0.6 g, 97%).

Workup

  1. stirringto stir at room temperature for 4 hours
  2. customIt was quenched with saturated ammonium chloride (20 mL)
  3. extractionextracted with diethyl ether (100 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo
  6. customto give a crude oil
  7. washSilica gel chromatography eluting with ethyl acetate in hexane (10–20%)

Sources & evidence

ORD record
ord-ead3c7fda41f4225bd651661312930dc
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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