Hydrochloric Acid → 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 324363Notes

Reaction equation

HRID 324363 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.O.[NH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.Cl.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:15]1[CH2:16][CH2:17][NH:12][CH2:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 871105-ChloroindoleHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chloro-1H-indole (25 g), piperidin-4-one, hydrate, hydrochloride (71 g), and potassium hydroxide (38 g) in ethanol (450 ml) was refluxed for 6 hours. After cooling inorganic salts were filtered off and ethanol evaporated in vacuo. To the remaining oil was added brine (500 ml) and ethyl acetate (2×200 ml). The organic phase was separated and worked-up as above. Yield of crude title product: 45 g (semicrystalline).

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureAfter cooling inorganic salts
  3. filtrationwere filtered off
  4. customethanol evaporated in vacuo
  5. additionTo the remaining oil was added brine (500 ml) and ethyl acetate (2×200 ml)
  6. customThe organic phase was separated

Sources & evidence

ORD record
ord-9d217abfacd344f19a447153eab2e03c
Source dataset
uspto-grants-2001_04
Patent number
US06218394B1

Reaction notes

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