Hydrochloric Acid → 9-bromo-6-[(3-chloropropyl)sulfanyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1764849노트

반응식

HRID 1764849 반응식
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[C:7]([NH:9]N)[CH:8]=1.O.[NH:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.Cl>CCO>[Br:2][C:3]1[C:8]2[C:19]3[CH2:18][NH:17][CH2:22][CH2:21][C:20]=3[NH:9][C:7]=2[C:6]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21584170Piperidin-4-one hydrateHCID 22735657HCID 22735657, 화합물

생성물 1

HCID 160642059-bromo-6-[(3-chloropropyl)sulfanyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole수율 58%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1-{5-Bromo-2-[(3-chloropropyl)sulfanyl]phenyl}hydrazine hydrochloride (784 mg, 2.4 mmol) and 4-piperidone monohydrate.HCl (398 mg, 2.6) were dissolved in EtOH (5mL). Conc. Hcl (0.2 mL, 2.4 mmol) were added. The reaction was refluxed for 18 hrs and then cooled to rt. The ppt was collected by filtration and the residue was washed with EtOH (3mL). 9-bromo-6-[(3-chloropropyl)sulfanyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloroide (500.4 mg, 58%) was isolated as a white powder. 1H NMR (CD3OD, 300 Mhz) δ7.18 (d, 1H, 8.0 Hz), 7.12 (d, 1H, 8.0 Hz), 4.73 (s, 2H), 3.64 (t, 2H, 6.6 Hz), 3.58 (t, 2H, 6.3 Hz), 3.16 (t, 2H, 6.3 Hz), 3.02 (t, 2H, 6.6 Hz), 1.87-1.96 (m, 2H) ppm.

후처리

  1. additionConc. Hcl (0.2 mL, 2.4 mmol) were added
  2. temperatureThe reaction was refluxed for 18 hrs
  3. filtrationThe ppt was collected by filtration
  4. washthe residue was washed with EtOH (3mL)

출처 및 근거

ORD 기록
ord-aa95bae0dcbf4865b31b541e766bcfe2
출처 데이터셋
uspto-grants-2007_06
특허 번호
USRE039679E1

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