HCID 19608103, compound → HCID 19607940, compound

HRID 745091Notes

Reaction equation

HRID 745091 reaction equation
[N:1]([CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:33])[C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[CH:19][CH:18]=2)[CH2:8][CH2:7][CH2:6]1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:33])[C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])=[CH:19][CH:18]=2)[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 19608103HCID 19608103, compound

Product 1

HCID 19607940HCID 19607940, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Azidomethyl-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.27 g) is suspended in ethanol (50 ml) and the mixture is subjected to catalytic hydrogenation at room temperature under 3 kg/cm2 for 6 hours by using 10% Pd-C (27 mg). The catalyst is removed by filtration with celite and the filtrate is distilled off and the resulting residue is recrystallized from ethanol to give 5-aminomethyl-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.12 g) as colorless needles, m.p. 233°-235° C.

Workup

  1. customThe catalyst is removed by filtration with celite
  2. distillationthe filtrate is distilled off
  3. customthe resulting residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-4ccbaeb683e44b288579025ccc5f7bfa
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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