Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Acetic Acid → 3-[(1,4-cis)-4-(4-Quinolin-5-yl-piperazin-1-yl)-cyclohexyl]-1H-indole-5-carbonitrile
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Acetic Acid | HCID 176 | — |
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Sodium triacetoxyborohydride | HCID 5049666 | — |
| 반응물 | 5-(Piperazin-1-yl)quinoline | HCID 10656226 | — |
| 반응물 | 3-(4-oxocyclohexyl)-1H-indole-5-carbonitrile | HCID 11241886 | — |
| 용매 | 1,1-Dichloroethane | HCID 6365 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 생성물 | 3-[(1,4-cis)-4-(4-Quinolin-5-yl-piperazin-1-yl)-cyclohexyl]-1H-indole-5-carbonitrile | HCID 25141218 | — |
반응 단계
To a solution of 5-(1-piperazinyl)-quinoline (500 mg, 2.35 mmol), 4-(5-cyano-1H-3-indolyl)-cyclohexanone (540 mg, 2.35 mmol), and sodium triacetoxyborohydride (740 mg, 3.5 mmol) in dichloroethane (20 mL) was added acetic acid (0.27 mL, 4.7 mmol) and stirred overnight at room temperature. The reaction was quenched with 1 M NaOH (50 mL) and extracted in CH2Cl2 (3×100 mL). The organic fractions were combined, dried over Na2SO4, concentrated, filtered and chromatographed (5% MeOH/EtOAc) yielding 410 mg (41%) of the cis isomer as a white solid. The HCl salt was generated from EtOAc yielding a white solid: mp 220-223° C.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US06465482B2 |
| 출처 데이터셋 | uspto-grants-2002_10 |
| ORD ID | ord-76f5d489dff64744919f798fd553ebdb |
| 출처 메모 | uspto-grants-2002_10 |