Homoveratrylamine → Bevantolol

HRID 1769826Notes

Reaction equation

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

Participants

Reactant 2

HCID 8421Homoveratrylamine

HCID 98180((m-Tolyloxy)methyl)oxirane2×

Product 1

HCID 2372Bevantolol

Procedure

When 3-(m-tolyloxy)-1,2-epoxypropane (hereinafter referred to as TOEP) represented by the following formula (2): ##STR2## reacts with β-(3,4 -dimethoxyphenyl) ethylamine (hereinafter referred to as HVA) represented by the following formula (3): ##STR3## to give bevantolol of the above formula (1), the resultant bevantolol further reacts with TOEP of the starting material to produce a by-product represented by the following formula (4): ##STR4## Such consumption of the produced bevantolol causes its low yield.

Sources & evidence

ORD record: ord-155583a4cbc74335b168e6e7f1805209
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382689

Reaction notes

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