5-Methoxytryptamine → 1-[2-(5-Methoxyindol-3-yl)ethyl]-4-(chroman-6-yl)piperazine

HRID 1733916Notes

Reaction equation

HRID 1733916 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][CH:5]=1.Cl[CH2:16][CH2:17][N:18]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[O:28][CH2:27][CH2:26][CH2:25]2)[CH2:19][CH2:20]Cl>>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]=[C:4]2[CH2:3][CH2:2][N:1]1[CH2:20][CH2:19][N:18]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[O:28][CH2:27][CH2:26][CH2:25]3)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 18335-MethoxytryptamineHCID 194388786-[N,N-bis(2-chloroethyl)amino]chroman

Product 1

HCID 194388661-[2-(5-Methoxyindol-3-yl)ethyl]-4-(chroman-6-yl)piperazine

Procedure

Analogously to Example 5, reaction of 3.2 g of 3-(2-aminoethyl)-5-methoxyindole with 1.3 equivalents of 6-[N,N-bis(2-chloroethyl)amino]chroman [obtainable by reaction of 2-chloroacetyl chloride with 6-aminochroman and subsequent reduction with diborane] gives 1-[2-(5-methoxyindol-3-yl)ethyl]-4-(chroman-6-yl)piperazine.

Sources & evidence

ORD record
ord-b588d417fcf641ceaa51e12a840033b0
Source dataset
uspto-grants-1996_07
Patent number
US05532241

Reaction notes

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