Claims
- 1. A method of preparing 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]-benzodiazepine comprising the following steps:
- A) preparing 2-amino-5-methylthiophene-3-carbonitrile by mixing sulfur, propional-dehyde in dimethyl formamide, then adding triethyl amine, then adding malononitrile;
- B) preparing 2-(2-nitroanilino)-5-methylthiophene-3-carbonitrile from the reaction product of step (A) by reaction with a slurry of sodium hydride dispersed in oil in tetrahydrofuran and 2-fluoro-nitrobenze;
- C) preparing 4-amino-2-methyl-10H-thiono[2,3-b][1,5]benzodiazepine hydrochloride from the reaction product of step (B) by reacting with a slurry of 2-(2-nitroanilino)-5-methyl-thiophene-3-carbonitrile in ethanol and a solution of anhydrous stannous chloride in hydrochloric acid;
- D) preparing 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine by refluxing the reaction product of step (C) with a mixture of N-methylpiperazine, dimethylsulphoxide and toluene.
CROSS REFERENCE
This application is a continuation-in-part of Ser. No. 08/387,997, filed Feb. 13, 1995, now U.S. Pat. No. 5,627,178, which was a continuation in part of application Ser. No. 08/044,844, filed Apr. 8, 1993, now abandoned, which was a continuation-in-part of application Ser. No. 07/890,348, filed May 22, 1992, which issued as U.S. Pat. No. 5,229,382, which was a continuation of Ser. No. 07/690,143, filed Apr. 23, 1991, now abandoned.
This application is also a divisional application of Ser. No. 08/748,292, filed on Nov. 13, 1996, now U.S. Pat. No. 5,817,655.
US Referenced Citations (1)
Number |
Name |
Date |
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5637584 |
Larsen |
Jun 1997 |
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Foreign Referenced Citations (1)
Number |
Date |
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454436 |
Oct 1991 |
EPX |
Non-Patent Literature Citations (1)
Entry |
Chakrabarti et. al., "4-Piperazinyl-10H-Thieno[2,3-b][1,5] Benzodiazepines as Potential Neuroleptics.", J. Med. Chem., vol. 23, No. 8, Aug. 1980, pp. 878-884. |
Divisions (1)
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Date |
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748292 |
Nov 1996 |
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Continuations (1)
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690143 |
Apr 1991 |
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Continuation in Parts (2)
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044844 |
Apr 1993 |
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Parent |
890348 |
May 1992 |
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