Piperidine → HCID 10275163, compound

HRID 1836123Notes

Reaction equation

HRID 1836123 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][C:7]=1[CH:15]=O.[CH3:18][NH:19][S:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:32])[CH2:26]2)(=[O:22])=[O:21].N1CCCCC1>C(O)C>[CH3:18][NH:19][S:20]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:32])/[C:26]/2=[CH:15]\[C:7]1[NH:8][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=2[C:6]=1[CH2:5][CH2:4][CH2:3][N:2]([CH3:17])[CH3:1])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10176909N-methyl-2-oxoindoline-5-sulfonamideHCID 112300633-(3-(Dimethylamino)propyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde

Product 1

HCID 10275163HCID 10275163, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(3-Dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (71 mg, 0.3 mmol), 5-methylaminosulfonyloxindole (68 mg, 0.3 mmol) and piperidine (0.03 ml) in 1 ml of ethanol was stirred at 60° C. for over night. The mixture was cooled and the solids collected by vacuum filtration and washed with ethanol to give (93 mg, 70% yield) of 3-[1-[3-(3-dimethylaminopropyl)-4,5,6,7-tetrahydro-1H-indol-2-yl]-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe solids collected by vacuum filtration
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-79dbf033942f422e91c5368bc8036f4b
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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