1-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-piperazine → HCID 11168397, compound

HRID 4952Notes

Reaction equation

HRID 4952 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[NH:8][CH:7]=1.[N:19]1([C:25]2[CH:34]=[CH:33][C:28]3[O:29][CH2:30][CH2:31][O:32][C:27]=3[CH:26]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(#N)C>[CH3:18][O:17][C:15]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][CH2:3][CH2:2][N:22]1[CH2:23][CH2:24][N:19]([C:25]2[CH:34]=[CH:33][C:28]3[O:29][CH2:30][CH2:31][O:32][C:27]=3[CH:26]=2)[CH2:20][CH2:21]1)=[O:16]

Participants

4

Reactant 2

HCID 10713381-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-piperazineHCID 14144805methyl 3-(4-chlorobutyl)-1H-indole-5-carboxylate

Product 1

HCID 11168397HCID 11168397, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.6 g of 3-(4-chlorobutyl)-5-methoxycarbonylindole [obtainable by reaction of 5-methoxycarbonylindole with 4-chlorobutyryl chloride to give 3-(4-chlorobutyryl)-5-methoxy indole and subsequent reduction with diborane to give 3-(4-chlorobutyl)-5-methoxycarbonylindole] and 3.4 g of 6-piperazino-1,4-benzodioxane ("A") in 200 ml of acetonitrile is stirred at room temperature for 14 hours and worked up in the conventional manner to give 6-[4-(4-(5-methoxycarbonyl indol-3-yl)butyl)piperazino]-1,4-benzodioxane, m.p. 177-179° (dihydrochloride).

Sources & evidence

ORD record
ord-fb73d2cc67f846e59ed64d19ad23ad56
Source dataset
uspto-grants-1993_09
Patent number
US05242925

Reaction notes

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