HCID 20233113, compound → Nerisopam

HRID 65447Notes

Reaction equation

HRID 65447 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:15]=3[CH2:14][C:13]([CH3:25])=[N:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O>CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:15]=3[CH2:14][C:13]([CH3:25])=[N:12][N:11]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 20233113HCID 20233113, compound

Product 1

HCID 65875Nerisopam

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×

Procedure

26.6 g (0.078 mole) of 1-(4-nitrophenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine are suspended in 540 ml of dimethylformamide, 2 g of 10% palladium on bone coal catalyst are suspended in 60 ml of dimethylformamide and added to the previous suspension. The reaction mixture is stirred vigorously at room temperature, under hydrogen. The reduction terminates in about 15 hours. Then the catalyst is filtered off, the filtrate is clarified with activated carbon and evaporated in vacuo. The crystalline residue is boiled with 250 ml of ethanol for one hour. Then it is cooled, the crystals are filtered off, washed twice with 30 ml of ethanol each and dried at 80° to 100° C.

Workup

  1. additionadded to the previous suspension
  2. filtrationThen the catalyst is filtered off
  3. customevaporated in vacuo
  4. waitThe crystalline residue is boiled with 250 ml of ethanol for one hour
  5. temperatureThen it is cooled
  6. filtrationthe crystals are filtered off
  7. washwashed twice with 30 ml of ethanol each and
  8. customdried at 80° to 100° C.

Sources & evidence

ORD record
ord-78f5f6c43f834862be9a65eeca725afa
Source dataset
uspto-grants-1986_09
Patent number
US04614740

Reaction notes

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