4-benzyl-N-methoxy-N-methylmorpholine-2-carboxamide → 1-(4-Benzyl-morpholin-2 yl)-pentan-1-one

HRID 30324Notes

Reaction equation

HRID 30324 reaction equation
CON(C)[C:4]([CH:6]1[O:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:5].[CH2:20]([Mg]Br)[CH2:21][CH2:22][CH3:23]>O1CCCC1>[CH2:12]([N:8]1[CH2:9][CH2:10][O:11][CH:6]([C:4](=[O:5])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:7]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 597893084-benzyl-N-methoxy-N-methylmorpholine-2-carboxamideHCID 178418682HCID 178418682, compound2×

Product 1

HCID 588548901-(4-Benzyl-morpholin-2 yl)-pentan-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 82 is prepared from 2 (0.87 g, 3.28 mmol) in anhydrous tetrahydrofuran (30 mL) and commercially available (Aldrich) n-butyl magnesium bromide (2M solution in THF, 5 mmol, 2.5 mL, 1.5 eq) following General Procedure 1. After stirring for 1 hour further n-butyl magnesium bromide (2M solution in THF, 1.6 mmol, 0.8 mL) is added and stirring continued for 30 minutes. The reaction is quenched by addition of ammonium chloride solution (30 mL) followed by EtOAc. The organic phases are combined, dried over magnesium sulphate and the solvent is removed in vacuo to give 82 (0.82 g, 96%). MW 261.37; C16H23NO2; LCMS (6 minute method): m/z 262.4 [M+H]+, RT 2.34 mm.

Workup

  1. additionis added
  2. customThe reaction is quenched by addition of ammonium chloride solution (30 mL)
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7ed7a8891b1a4448a61d2d6a4bb7ad15
Source dataset
uspto-grants-2008_09
Patent number
US07423037B2

Reaction notes

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