HCID 16110284, compound → HCID 16110221, compound

HRID 900814Notes

Reaction equation

HRID 900814 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([N+:25]([O-])=O)=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[NH2:25][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:14]([N:11]1[CH2:12][CH2:13][CH:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]1)=[O:15])=[CH:24]2

Participants

4

Reactant 1

HCID 16110284HCID 16110284, compound

Product 1

HCID 16110221HCID 16110221, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.5 g (1.38 mmol) of 1-(4-benzylpiperidine-1-yl)-1-(5-nitro-1H-indole-2-yl)methanone, 20 ml of methanol and 0.1 g of 10% Pd/C catalyst is hydrogenated for 5 h. The catalyst is filtered off, washed with methanol and the filtrate is concentrated. The residue is treated with diethylether and the precipitated crystals are filtered off to yield 0.27 g (59%) of the title compound. Mp.: 175-180° C. (diethylether).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol
  3. concentrationthe filtrate is concentrated
  4. additionThe residue is treated with diethylether
  5. filtrationthe precipitated crystals are filtered off

Sources & evidence

ORD record
ord-5f648b0cf1cc440884a3cbdd434189b6
Source dataset
uspto-grants-2008_04
Patent number
US07361670B2

Reaction notes

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