2-ethyl-5-(4-hydrazino-4-oxobutoxy)-1-(phenylmethyl)-1H-indole-3-acetamide → 5-(4-amino-4-oxobutoxy)-2-ethyl-1-(phenylmethyl)-1H-indole-3-acetamide

HRID 1069614Notes

Reaction equation

HRID 1069614 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:5]2[C:10]([C:11]=1[CH2:12][C:13]([NH2:15])=[O:14])=[CH:9][C:8]([O:16][CH2:17][CH2:18][CH2:19][C:20]([NH:22]N)=[O:21])=[CH:7][CH:6]=2)[CH3:2].CO.CCOC(C)=O>C(O)C.[Ni]>[NH2:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][O:16][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3]([CH2:1][CH3:2])=[C:11]2[CH2:12][C:13]([NH2:15])=[O:14]

Participants

5

Reactant 2

HCID 211918472-ethyl-5-(4-hydrazino-4-oxobutoxy)-1-(phenylmethyl)-1H-indole-3-acetamideHCID 21584119Ethylacetate methanol

Product 1

HCID 155518595-(4-amino-4-oxobutoxy)-2-ethyl-1-(phenylmethyl)-1H-indole-3-acetamideYield 47.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 150 mg (0.37 mmol) of 2-ethyl-5-(4-hydrazino-4-oxobutoxy)-1-(phenylmethyl)-1H-indole-3-acetamide and 200 mg of Raney Ni in 15 mL of ethanol was heated to maintain reflux for 2 hours. After cooling, the EtOH was poured off and the Raney Ni washed twice with methylene chloride. The combined washes were filtered, concentrated at reduced pressure and the residue chromatographed on silica eluting with EtOAc, then 10% MeOH/EtOAc to give 69 mg (47% yield) of 5-(4-amino-4-oxobutoxy)-2-ethyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp 176-179° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 2 hours
  4. temperatureAfter cooling
  5. washthe Raney Ni washed twice with methylene chloride
  6. filtrationThe combined washes were filtered
  7. concentrationconcentrated at reduced pressure
  8. customthe residue chromatographed on silica eluting with EtOAc

Sources & evidence

ORD record
ord-a71986e42c52496092d35e8902dea8c0
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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