Hydrochloric Acid → 5-Nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole--hydrogen chloride (1/1)
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[ClH:13].Cl.[NH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1>C(O)C>[ClH:13].[NH:15]1[CH2:16][CH:17]=[C:18]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][CH:8]=2)[CH2:19][CH2:20]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 7.7 g of 5-nitro-1H-indole and 225 ml of ethanol saturated with hydrogen chloride and 22.5 g of the hydrate of 4-piperidone hydrochloride was refluxed for 3 hours under a nitrogen atmosphere and the mixture was then stirred at room temperature for one hour and at 0° C. for another hour. The mixture was filtered and the recovered product was rinsed with iced ethanol, with ethyl acetate and ether to obtain 14 g of raw product. The latter was crystallized from 600 ml of 1-1 methanol-water mixture and after standing overnight at 0° to 5° C., the mixture was filtered. The product was rinsed with methanol and dried to obtain 9.8 g of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-5-nitro-1H-indole hydrochloride melting at 275° C.
Workup
- temperaturewas refluxed for 3 hours under a nitrogen atmosphere
- filtrationThe mixture was filtered
- washthe recovered product was rinsed with iced ethanol, with ethyl acetate and ether
- customto obtain 14 g of raw product
- customThe latter was crystallized from 600 ml of 1-1 methanol-water mixture
- waitafter standing overnight at 0° to 5° C.
- filtrationthe mixture was filtered
- washThe product was rinsed with methanol
- customdried
Sources & evidence
- ORD record
- ord-0976de28b91142c1a88c9d6aa969848f
- Source dataset
- uspto-grants-1982_04
- Patent number
- US04324790
Reaction notes
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