Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Thionyl Chloride → (+/-)-N,N-diethyl-4-((alphaR*)-3-hydroxy-alpha-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)benzyl)benzamide
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Thionyl Chloride | HCID 24386 | — |
| 반응물 | 2,5-Dimethylpiperazine, trans- | HCID 220672 | — |
| 반응물 | Tetraethylammonium fluoride hydrate | HCID 16211652 | — |
| 반응물 | 4-((3-((Tert-butyldimethylsilyl)oxy)phenyl)(hydroxy)methyl)-N,N-diethylbenzamide | HCID 22350014 | — |
| 생성물 | (+/-)-N,N-diethyl-4-((alphaR*)-3-hydroxy-alpha-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)benzyl)benzamide | HCID 18665077 | — |
반응 단계
4-(3-(tert-Butyldimethylsilyloxy)-α-hydroxybenzyl)-N,N-diethylbenzamide (Example 1, infra) was treated with thionyl chloride and trans-2,5-dimethylpiperazine as described in Example 5. The crude mixture of diastereomers was purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.25:0.1). The less mobile isomer (1.28 g, 2.5 mmol) was dissolved in acetonitrile and treated with tetraethylammonium fluoride hydrate (0.6 g, 4.0 mmol) as in Example 7 to give 0.46 g of (±)-N,N-diethyl-4-((αR*)-3-hydroxy-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)benzyl)benzamide as a white solid, mp 175-177° C.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US06919350B2 |
| 출처 데이터셋 | uspto-grants-2005_07 |
| ORD ID | ord-ea780c10ea604e4d81e3dc5ff792b861 |
| 출처 메모 | uspto-grants-2005_07 |