Ethanol → 1'-Acetyl-5,6-dihydrospiro[1H-indolo[3,2-c]quinoline-6,4'-piperidine]

HRID 727771Notes

Reaction equation

HRID 727771 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.C(O)C.[C:20]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)(=[O:22])[CH3:21]>C(O)(=O)C>[C:20]([N:23]1[CH2:28][CH2:27][C:26]2([C:16]3=[C:15]4[C:10](=[N:9][C:8]3=[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH2:4]3)[NH:1]2)[CH:11]=[CH:12][CH:13]=[CH:14]4)[CH2:25][CH2:24]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 122563N-Acetyl-4-piperidoneHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 198249201'-Acetyl-5,6-dihydrospiro[1H-indolo[3,2-c]quinoline-6,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution prepared from 5 g of 2-(2-aminophenyl)indole, 100 ml of ethanol and 2 ml of glacial acetic acid was added dropwise 3 ml of 1-acetyl-4-piperidone. The resultant solution was refluxed for 6 hours and thereafter cooled, whereupon a solid precipitated. Filtration and washing with ether and hexane gave 3.95 g of yellow solid, m.p. 285°-287° dec.

Workup

  1. temperaturecooled, whereupon a solid
  2. customprecipitated
  3. filtrationFiltration
  4. washwashing with ether and hexane

Sources & evidence

ORD record
ord-4de7026fa48442c9a28ce5fcb3dc2eea
Source dataset
uspto-grants-1991_09
Patent number
US05045539

Reaction notes

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