1-Benzyl-4-piperidone → 3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-5-bromo-1H-indole

HRID 358593Notes

Reaction equation

HRID 358593 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2>[OH-].[K+].CO>[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[C:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][CH:12]=1

Participants

5

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 249055-Bromoindole

Product 1

HCID 143926503-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-5-bromo-1H-indoleYield 90.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

Freshly distilled 1-Benzyl-4-piperidone (11.7 g) was added to a stirred solution of 5-bromoindole (11.0 g) in 2M potassium hydroxide in methanol (81ml). The mixture was stirred at reflux for 8 h and then allowed to cool to 25° over 8 h. The solid was collected by filtration, washed with a mixture of methanol:water (2:1, 2×15 ml) and dried in vacuo at 50° for 18 h to give the title compound as a crystalline solid (18.6 g) m.p. 173°-175° (decomp).

Workup

  1. temperatureat reflux for 8 h
  2. temperatureto cool to 25° over 8 h
  3. filtrationThe solid was collected by filtration
  4. washwashed with a mixture of methanol:water (2:1, 2×15 ml)
  5. customdried in vacuo at 50° for 18 h

Sources & evidence

ORD record
ord-34862dc0a22f4a8cbe881ab32a0e1dab
Source dataset
uspto-grants-1991_03
Patent number
US04997841

Reaction notes

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