HCID 19734231, compound → HCID 182591, compound

HRID 327078Notes

Reaction equation

HRID 327078 reaction equation
[CH2:1]([N:8]([CH2:10][CH:11]1[C:17]2=[CH:18][NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[C:15]([C:16]=32)[C:14](=[O:24])[NH:13][CH2:12]1)C)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:1][NH:8][CH2:10][CH:11]1[C:17]2=[CH:18][NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[C:15]([C:16]=32)[C:14](=[O:24])[NH:13][CH2:12]1

Participants

5

Reactant 2

HCID 19734231HCID 19734231, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 182591HCID 182591, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.38 g of 3-(N-benzyl-N-methylaminomethyl)-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole (see Example 3 for preparation) were dissolved in 150 ml of methanol. A spatula tip of a palladium/carbon catalyst (10%) was added to the solution under a stream of nitrogen. The mixture was subsequently hydrogenated in an autoclave under a hydrogen pressure of 3.5 bar at a temperature of 50° C. while stirring. After 3 hours the hydrogen was discharged, the reaction mixture was flushed with nitrogen and the catalyst was filtered out. The remaining solution was evaporated and the oily crude product remaining as residue was purified by low pressure chromatography on silica gel using methanol/25% strength aqueous ammonia solution 96:4 as eluent. 0.9 g of 3-methylaminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole was obtained as a foam-like product.

Workup

  1. customat a temperature of 50° C.
  2. customthe reaction mixture was flushed with nitrogen
  3. filtrationthe catalyst was filtered out
  4. customThe remaining solution was evaporated
  5. customwas purified by low pressure chromatography on silica gel

Sources & evidence

ORD record
ord-0641e38bee4249fba45d5cfa14c274c9
Source dataset
uspto-grants-1993_12
Patent number
US05272143

Reaction notes

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