Doxazosin → Doxazosin Monohydrochloride

HRID 1969338Notes

Reaction equation

HRID 1969338 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14]([NH2:15])=[N:13][C:12]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([CH:24]4[O:33][C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[O:26][CH2:25]4)=[O:23])[CH2:18][CH2:17]3)=[N:11][C:6]2=[CH:7][C:8]=1[O:9][CH3:10].O1C(C(N2CCNCC2)=O)COC2C=CC=CC1=2.[Cl:52]C1N=C(N)C2C(=CC(OC)=C(OC)C=2)N=1>C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14]([NH2:15])=[N:13][C:12]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([CH:24]4[O:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[O:26][CH2:25]4)=[O:23])[CH2:18][CH2:17]3)=[N:11][C:6]2=[CH:7][C:8]=1[O:9][CH3:10].[ClH:52]

Participants

5

Reactant 3

HCID 3157DoxazosinHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 2735449N-1,4-Benzodioxane-2-carbonyl piperazine

Product 1

HCID 11591230Doxazosin Monohydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Organic Preparations and Procedures International (2003); 35; 603-608 describes the procedure for synthesizing doxazosin by treating (2,3-dihydrobenzo[b][1,4]dioxin-2-yl) (piperazin-1-yl)methanone with 2-chloro-6,7-dimethoxy quinazolin-4-amine in presence of n-butanol to obtain doxazosin hydrochloride; which on further treatment with aqueous ammonia solution yields doxazosin base.

Sources & evidence

ORD record
ord-c9baeff231494017b337b490b2b22b32
Source dataset
uspto-grants-2013_04
Patent number
US08426590B2

Reaction notes

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