1,3-Benzodioxole, 5-(chloromethyl)- → 2,2-diphenyl-5-[N-(3,4-methylenedioxybenzyl)-N-methylamino]pentanamide

HRID 1463852Notes

Reaction equation

HRID 1463852 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][NH:14][CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22]1[O:32][C:31]2[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][C:24]=2[O:23]1.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH2:27][C:26]2[CH:29]=[CH:30][C:31]3[O:32][CH2:22][O:23][C:24]=3[CH:25]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 516892Sodium BicarbonateHCID 190884752,2-Diphenyl-5-methylaminopentanamide

Product 1

HCID 539168912,2-diphenyl-5-[N-(3,4-methylenedioxybenzyl)-N-methylamino]pentanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (0.29 g--see Preparation 3), 3,4-methylenedioxybenzyl chloride (0.18 g--commercially available), sodium bicarbonate (0.1 g) and acetonitrile (20 ml) was heated under reflux for 3 hours. The mixture was partitioned between dichloromethane and 10% aqueous sodium carbonate, the layers separated and the dichloromethane layer dried (MgSO4). The solution was concentrated in vacuo and the residue purified by column chromatography on silica, eluting with dichloromethane containing methanol (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 0.22 g.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe mixture was partitioned between dichloromethane and 10% aqueous sodium carbonate
  3. customthe layers separated
  4. dry with materialthe dichloromethane layer dried (MgSO4)
  5. concentrationThe solution was concentrated in vacuo
  6. customthe residue purified by column chromatography on silica
  7. washeluting with dichloromethane
  8. additioncontaining methanol (0% up to 6%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa68c66c98554658bf6bf561c5447f24
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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