Ethanol → 5-(4,5-dihydrothiazol-5-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1003591Notes

Reaction equation

HRID 1003591 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1)#N.[SH:19][CH2:20][CH2:21][NH2:22].[CH2:23](O)C>>[S:19]1[CH:20]([C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][CH:11]=2)[NH:8][CH:7]=[C:6]3[C:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=2)[CH2:21][N:22]=[CH:23]1

Participants

4

Reactant 3

HCID 702EthanolHCID 6058CysteamineHCID 149732163-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile

Product 1

HCID 187971695-(4,5-dihydrothiazol-5-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 51%

Procedure

A mixture of 1.0 gm (4.2 mMol) 5-cyano-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and 0.90 gm (11.7 mMol) 2-mercaptoethylamine in 20 mL ethanol was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and a colorless crystalline solid formed. The solid was isolated by filtration, washed with ethanol and dried under reduced pressure to provide 0.64 gm (51%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. customa colorless crystalline solid formed
  4. customThe solid was isolated by filtration
  5. washwashed with ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e52a4bc462944199835d2ce544719e0e
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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