Acetate → 6-acetylamino-1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepine

HRID 2051190Notes

Reaction equation

HRID 2051190 reaction equation
C([O-])(=O)C.[C:5]([NH:8][CH:9]1[CH2:15][N:14]([CH3:16])[CH2:13][CH2:12][NH:11][CH2:10]1)(=[O:7])[CH3:6].[CH3:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[C:5]([NH:8][CH:9]1[CH2:10][N:11]([CH2:17][C:18]2[CH:25]=[CH:24][CH:23]=[C:20]([CH3:21])[CH:19]=2)[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15]1)(=[O:7])[CH3:6]

Participants

7

Reactant 5

HCID 175AcetateHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12102m-Xylyl chlorideHCID 152061556-acetylamino-1-methylhexahydro-1H-1,4-diazepine

Product 1

HCID 149989916-acetylamino-1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of acetate of 6-acetylamino-1-methylhexahydro-1H-1,4-diazepine (3.0 g), 3-methylbenzyl chloride (3.5 g), potassium carbonate (17 g), sodium iodide (0.1 g) and methyl ethyl ketone (200 ml) is refluxed with stirring for 16 hours. The reaction mixture is filtered, and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel with elution of chloroform-methanol (20:1). Fractions containing the title compound are pooled and evaporated under reduced pressure to give the title compound as an oil.

Workup

  1. temperatureis refluxed
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is chromatographed on silica gel with elution of chloroform-methanol (20:1)
  5. additionFractions containing the title compound
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-161e1459819447a382ea4a9b1a0dabaf
Source dataset
uspto-grants-1991_05
Patent number
US05017573

Reaction notes

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