Triethylamine → Indole

HRID 867011Notes

Reaction equation

HRID 867011 reaction equation
BrCC[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.CC1C=C(C=CC=1C)C(C1CCNCC1)=O.C(N(CC)CC)C>CN(C)C=O>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 769243-(2-Bromoethyl)indoleHCID 13180309HCID 13180309, compound

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9.6 g of 3-(2-bromoethyl)indole, 11.5 g of 4-(3,4-dimethylbenzoyl)piperidine hydrochloride and 10.1 g of triethylamine in 300 ml of dimethylformamide is treated according to the manipulative procedure described in Example 3(b) to give an indole, which is purified on a silica gel column, eluted with 5% methanol-benzene mixture and recrystallized from an ethanol-water mixture to give the solid, mp 172°-173° C., 3-{2-[4-(3,4-dimethylbenzoyl)piperidyl]ethyl}indole.

Sources & evidence

ORD record
ord-8100118767f54c1cb5a2c1bfd8dd39bc
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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