One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities

Yu, Wen-Shuai; Wu, Zenong; Qiu, Zengfeng; Zhao, Chunjie; Zhang, Fuli; Yang, Zhezhou

doi:10.1134/s1070428020070258

Cited by 2 publications

(4 citation statements)

References 9 publications

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“…It was reported in our previous work that papaverine hydrochloride could be synthesized from 2-(3,4-dimethoxyphenyl)ethanamine ( 2 ) and 3,4-dimethoxybenzeneacetic acid ( 3 ) through a one-pot method . Based on our previous research, a one-pot process to synthesize 1 .HCl using the same materials was proposed.…”

Section: Resultsmentioning

confidence: 99%

“…It was reported in our previous work that papaverine hydrochloride could be synthesized from 2-(3,4dimethoxyphenyl)ethanamine (2) and 3,4-dimethoxybenzeneacetic acid (3) through a one-pot method. 25 Based on our previous research, a one-pot process to synthesize 1.HCl using the same materials was proposed. First, 4 with >94% purity, as monitored by high-performance liquid chromatography (HPLC), was prepared by condensation of 3 and 2 in xylene at 150 °C for 17 h. The total proportion of 3 and 2 was less than 5%.…”

Section: ■ Introductionmentioning

confidence: 99%

“…It was suggested by previous research that the base of 5 is easily oxidized in air easily. 25 Therefore, the reduction reaction was allowed to occur in the EtOH and aqueous 5.HCl mixture in NaOH/NaBH 4 under a N 2 atmosphere to avoid oxidation and impurity generation. The purity of tetrahydropapaverine (1) was up to 92% after the reduction reaction.…”

Section: ■ Introductionmentioning

confidence: 99%

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Practical Process for synthesizingR-Tetrahydropapaverine─A Key Intermediate of Cisatracurium Besylate (Nimbex)

Peng

Zheng

et al. 2022

Org. Process Res. Dev.

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In this paper, a practical process to synthesize the key intermediate R-tetrahydropapaverine of cisatracurium besylate was proposed. First, tetrahydropapaverine hydrochloride (1.HCl) was prepared from inexpensive and commercially available 2-(3,4-dimethoxyphenyl)ethanamine (2) and 3,4-dimethoxybenzeneacetic acid (3) through a one-pot process. The yield and purity of the product were up to 85.4 and 98.1% on a 150 g scale, respectively. Then, a new resolution process was developed to prepare R-tetrahydropapaverine by using a half equivalent of N-acetyl-d-phenylalanine, and the obtained R-tetrahydropapaverine had a yield of 28.1% and 98.0% ee on a 120 g scale. Furthermore, the S-isomer was racemized to 1.HCl in the one-pot process with 77.7% isolated yield and 99.0% purity.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Practical Process for synthesizingR-Tetrahydropapaverine─A Key Intermediate of Cisatracurium Besylate (Nimbex)

Peng

Zheng

et al. 2022

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…Isoquinolines represent important structural motifs frequently found in natural products, functional materials and pharmaceuticals. 1 Their unusual bioactive properties, such as antispasmodic, 2 antiinflammatory, 3 antihypertensive 4 and antitumour 5 activities, have attracted much attention ( Fig. 1 ).…”

Section: Introductionmentioning

confidence: 99%