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Triethylamine → Terazosin

HRID 619669
Notes
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Reaction equation

HRID 619669 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.C(N(CC)CC)C.[O:29]1[CH2:33][CH2:32][CH2:31][CH:30]1[C:34](Cl)=[O:35]>C(Cl)Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:2]([NH2:1])=[N:3][C:4]([N:16]3[CH2:21][CH2:20][N:19]([C:34]([CH:30]4[O:29][CH2:33][CH2:32][CH2:31]4)=[O:35])[CH2:18][CH2:17]3)=[N:5][C:6]2=[CH:7][C:8]=1[O:14][CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 551254Tetrahydro-2-furancarbonyl chlorideHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 5401TerazosinYield 154.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

37.6 g 4-amino-2-(1-piperazinyl)-6,7-dimethoxyquinazoline and 15.8 g triethylamine are suspended in 400 ml methylene chloride. The suspension is cooled to -5° C. This suspension is stirred while 21.0 g tetrahydrofuran-2-carboxylic acid chloride are added drop by drop. The suspension is continued to be stirred for two hours at 0° C., thereafter the solvent is distilled off under vacuum. 200 ml methanol and 200 ml acetone are added to the residue. The resulting suspension is kept under reflux for 0.5 hours while stirring. Thereafter, it is cooled to 0° C. The product is isolated by filtration. 78 g of moist terazosin base are obtained.

Workup

  1. additionare added drop by drop
  2. distillationthe solvent is distilled off under vacuum
  3. addition200 ml methanol and 200 ml acetone are added to the residue
  4. temperatureunder reflux for 0.5 hours
  5. stirringwhile stirring
  6. temperatureThereafter, it is cooled to 0° C
  7. customThe product is isolated by filtration

Sources & evidence

ORD record
ord-30e79277aa3a428797898df30a3543a7
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05959108

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes