Chloroacetyl chloride → 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

HRID 398265Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:17][CH3:18])=[C:7]([CH:9]([OH:16])[CH2:10][NH:11][C:12]([CH2:14]N)=[O:13])[CH:8]=1.Cl.[Cl:20]CC(Cl)=O>>[Cl:20][CH2:14][C:12]([NH:11][CH2:10][CH:9]([C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[O:17][CH3:18])[OH:16])=[O:13]

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 18340Midodrine hydrochloride

Product 1

HCID 113578062-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

Procedure

The synthesis of Midodrine HCl consists of reacting the key intermediate (2) with chloroacetyl chloride to afford 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide (3). The reaction of (3) with sodium azide will provide 2-azido-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide (4) which is subsequently subjected to hydrogenation to afford Midodrine base (6).

Sources & evidence

ORD record: ord-224076de90a54dcca9a3d01e0dc9c907
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610886B2

Reaction notes

Loading…