Piperonal → 3-(3-{[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

HRID 2300539Notes

Reaction equation

HRID 2300539 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH2:14])[CH:8]=1.[O:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]=O)=[CH:24][C:19]=2[O:18][CH2:17]1>CO>[CH3:2][O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH:14][CH2:25][C:23]2[CH:22]=[CH:21][C:20]3[O:16][CH2:17][O:18][C:19]=3[CH:24]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 8438PiperonalHCID 22282736Methyl 3-(3-(aminomethyl)phenyl)propanoate hydrochloride

Product 1

HCID 540353743-(3-{[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-methyl}-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Step A was prepared from 3-(3-aminomethyl-phenyl)-propionic acid methyl ester hydrochloride salt, of Preparation 44, and benzo[1,3]dioxole-5-carbaldehyde using the method described in Example 1, Step A except the imine was formed in MeOH at reflux over 4 h. 1H NMR (400 MHz, CDCl3) δ 7.27-6.74 (m, 7H), 5.90 (s, 2H), 3.77 (s, 2H), 3.71 (s, 2H), 3.64 (s, 3H), 2.92 (t, 2H), 2.62 (t, 2H); MS 328 (M+1).

Workup

  1. temperatureat reflux over 4 h

Sources & evidence

ORD record
ord-c0fc114180b248bc9f7a85696994b164
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

Loading…