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

HRID 1277650Notes

Reaction equation

HRID 1277650 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.Cl.O.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[OH-].[K+]>O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:17]3[CH2:18][CH2:19][NH:14][CH2:15][CH:16]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 766596-Methoxy-1H-indoleHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 130190056-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 g of 6-methoxy-1H-indole, 41.75 g of the hydrochloride of 4-piperidone monohydrate and 205 ml of methanolic 2 N potassium hydroxide was refluxed for 81/2 hours and was then stirred overnight at room temperature. The mixture was slowly diluted with water to a volume of 1.2 liters and crystallization was effected. The mixture was stirred for 30 minutes and was filtered and the recovered product was carefully rinsed with water and dried to obtain 23.05 g of 6-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole melting at 193°-194° C.

Workup

  1. temperaturewas refluxed for 81/2 hours
  2. stirringThe mixture was stirred for 30 minutes
  3. filtrationwas filtered
  4. washthe recovered product was carefully rinsed with water
  5. customdried

Sources & evidence

ORD record
ord-2cfccc9c39b240138abe7b6eea45f5f9
Source dataset
uspto-grants-1981_07
Patent number
US04278677

Reaction notes

Loading…