Sodium Azide → 2-azido-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

HRID 1278959Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[OH:8])=[O:4].[N-:19]=[N+:20]=[N-:21].[Na+]>>[N:19]([CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[OH:8])=[O:4])=[N+:20]=[N-:21]

Participants

Reactant 2

HCID 33557Sodium Azide

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

Product 1

HCID 115943302-azido-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-47b66346050a4f55a69b09400c741703
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444851B1

Reaction notes

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