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

HRID 1764849ノート

反応式

HRID 1764849 の反応式
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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21584170Piperidin-4-one hydrateHCID 22735657HCID 22735657、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-aa95bae0dcbf4865b31b541e766bcfe2
出典データセット
uspto-grants-2007_06
特許番号
USRE039679E1

反応ノート

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