1-Piperazinecarboxaldehyde → (2S)-(-)-1-(4-indolyloxy)-3-(4-(formyl)piperazin-1-yl)-2-propanol

HRID 565451Notes

Reaction equation

HRID 565451 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16]>CO>[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:20]3[CH2:21][CH2:22][N:17]([CH:15]=[O:16])[CH2:18][CH2:19]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

4

Reactant 2

HCID 821911-PiperazinecarboxaldehydeHCID 10943254(2s)-Glycidyl indol-4-yl ether

Product 1

HCID 15895685(2S)-(-)-1-(4-indolyloxy)-3-(4-(formyl)piperazin-1-yl)-2-propanolYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 1-formylpiperazine in 86% yield. mp 106-107°. FDMS m/e=303 (M+ of free base). α[D]589=−1.98 (c=1.0, methanol).

Sources & evidence

ORD record
ord-7e53b40d5bb44f148f5b3324ed6c7b28
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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