HCID 13520518, compound → HCID 70453449, compound

HRID 1380582Notes

Reaction equation

HRID 1380582 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[NH:14][C:15]2[C:20]([C:21]=1[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:19][CH:18]=[CH:17][CH:16]=2>[Ni].CO>[NH2:5][C:4]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[C:3]([C:13]1[NH:14][C:15]2[C:20]([C:21]=1[CH2:22][CH2:23][CH2:24][N:25]([CH3:26])[CH3:27])=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:2](=[O:6])[CH3:1]

Participants

4

Reactant 1

HCID 13520518HCID 13520518, compound

Product 1

HCID 70453449HCID 70453449, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3.6 grams (0.01 mole) of 2-(5-methyl-3-phenyl-4-isoxazolyl)-3-(3-dimethylamino propyl)-1H-indole and 0.75 grams of Raney nickel in 75 milliliters of methanol is hydrogenated at 50 psi and 25° C. until thin layer chromatography shows no remaining starting material (18 hours). The mixture is filtered through celite and the celite washed with methanol. The combined methanol filtrates are evaporated in vacuo, and the resulting oil is crystallized from ethanol to give 4-amino-3-[3-(3-dimethylamino propyl)-1H-indol-2-yl]-4-phenyl-3-buten-2-one, (m.p. 268°-269° C.).

Workup

  1. customis hydrogenated at 50 psi and 25° C. until thin layer chromatography shows
  2. customno remaining starting material (18 hours)
  3. filtrationThe mixture is filtered through celite
  4. washthe celite washed with methanol
  5. customThe combined methanol filtrates are evaporated in vacuo
  6. customthe resulting oil is crystallized from ethanol

Sources & evidence

ORD record
ord-9e1f509e73194c5dbfe6a25d61267a0e
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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