Ethanol → 2-Methyl-3-{2-[4-(4-toluyl)piperidyl]ethyl}indole

HRID 2420514Notes

Reaction equation

HRID 2420514 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH3:13].[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(O)C>CN(C)C=O>[CH3:13][C:5]1[NH:6][C:7]2[C:12]([C:4]=1[CH2:3][CH2:2][N:23]1[CH2:24][CH2:25][CH:20]([C:17]3[CH:16]=[CH:15][C:14]([CH3:26])=[CH:19][CH:18]=3)[CH2:21][CH2:22]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 3

HCID 702EthanolHCID 5447514-(4-Methylphenyl)piperidineHCID 153237653-(2-Bromoethyl)-2-methyl-1H-indole

Product 1

HCID 203117222-Methyl-3-{2-[4-(4-toluyl)piperidyl]ethyl}indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 11.8 g of 3-(2-bromoethyl)-2-methylindole, 20.3 g of 4-(4-toluyl)piperidine [Example 5(a)] in 500 ml of dimethylformamide is treated according to the manipulative procedure described in Example 3(b) to give the off-white solid, mp 192°-194° C., 2-methyl-3-{2-[4-(4-toluyl)piperidyl]ethyl}indole from ethanol.

Sources & evidence

ORD record
ord-499c08d2ae3d44c994490cf19c512038
Source dataset
uspto-grants-1978_08
Patent number
US04110459

Reaction notes

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