Water → 3-{2-[4-(2-Toluyl)piperidyl]ethyl}indole

HRID 867022Notes

Reaction equation

HRID 867022 reaction equation
Cl.[C:2]1([CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C.Br[CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1.O>CN(C)C=O>[C:2]1([CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][N:11]([CH2:23][CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 769243-(2-Bromoethyl)indoleHCID 219369564-(2-Methylphenyl)piperidine hydrochloride

Product 1

HCID 203117013-{2-[4-(2-Toluyl)piperidyl]ethyl}indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 4.2 g of 4-(2-toluyl)piperidine hydrochloride and 4.0 g of triethylamine in 150 ml of dimethylformamide is added 3.8 g of 3-(2-bromoethyl)indole. The resulting solution is stirred at ambient temperature for 70 hours and stirring is continued while 500 ml of water are added dropwise. An oil appears which is extracted from the solution with chloroform, the combined chloroform extracts are dried and the excess chloroform is removed, leaving an oil which crystallizes upon standing. The solid product is recrystallized from cyclohexane and then twice from an ethanol-water mixture to give flakes, mp 111°-112° C., 3-{2-[4-(2-toluyl)piperidyl]ethyl}indole.

Workup

  1. stirringstirring
  2. additionare added dropwise
  3. extractionis extracted from the solution with chloroform
  4. dry with materialthe combined chloroform extracts are dried
  5. customthe excess chloroform is removed
  6. customleaving an oil which
  7. customcrystallizes
  8. customThe solid product is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-576db3d10cd6490eade9423e7c8fa8da
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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