Chloroacetyl chloride → 3-(Chloroacetyl)-1H-indole-5-carbonitrile
Reaction equation
NCCC1C2C(=CC=C(C#N)C=2)NC=1.[C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)#[N:16].[Cl:26][CH2:27][C:28](Cl)=[O:29]>>[Cl:26][CH2:27][C:28]([C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([C:15]#[N:16])[CH:18]=2)[NH:22][CH:21]=1)=[O:29]Participants
4
Procedure
A mixture of 2.6 g of 3-(2-aminoethyl)-5-cyanoindole [obtainable by reaction of 5-cyanoindole with 2-chloroacetyl chloride to give 3-(2-chloroacetyl)-5-cyanoindole, subsequent reduction with diborane, reaction with phthalimide and hydrolysis]and one equivalent of 5-[N,N-bis(2-chloroethyl)amino]benzofuran [obtainable by reaction of 2-chloroacetyl chloride with 5-aminobenzofuran and subsequent reduction with diborane] in 40 ml of acetone and 40 ml of water is boiled for 20 hours and then worked up in the customary manner. 1-[2-(5-Cyanoindol-3-yl)ethyl]-4-(benzofuran-5-yl)piperazine is obtained.
Sources & evidence
- ORD record
- ord-2342fa222038480ab253499ec9e85b6d
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05532241
Reaction notes
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