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

HRID 50973Notes

Reaction equation

HRID 50973 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:10][CH2:11][CH2:12][CH2:13][Cl:14])=[C:6]([NH:8]N)[CH:7]=1.O.[NH:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.Cl>CCO>[Br:1][C:2]1[C:7]2[C:18]3[CH2:17][NH:16][CH2:21][CH2:20][C:19]=3[NH:8][C:6]=2[C:5]([S:10][CH2:11][CH2:12][CH2:13][Cl:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21584170Piperidin-4-one hydrateHCID 227356581-{5-Bromo-2-[(3-chloropropyl)sulfanyl]phenyl}hydrazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-{5-Bromo-2-[(3-chloropropyl)sulfanyl]phenyl}hydrazine hydrochloroide (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.

Workup

  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)

Sources & evidence

ORD record
ord-e006649c94cd4ab38c3e914c5021f497
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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