Hydrochloric Acid → 3-chloropropyl 9-nitro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl sulfide

HRID 50962Notes

Reaction equation

HRID 50962 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15]N.O.[NH:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.Cl>C(O)C(F)(F)F>[N+:12]([C:9]1[C:8]2[C:20]3[CH2:19][NH:18][CH2:23][CH2:22][C:21]=3[NH:15][C:7]=2[C:6]([S:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:11][CH:10]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21584170Piperidin-4-one hydrateHCID 227354561-{2-[(3-Chloropropyl)sulfanyl]-5-nitrophenyl}hydrazine

Product 1

HCID 160642073-chloropropyl 9-nitro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl sulfideYield 96.9%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

1-{2-[(3-Chloropropyl)sulfanyl]-5-nitrophenyl}hydrazine (100 mg, 0.38 mmol) and 4-piperidone mono hydrate (58 mg, 0.38 mmol) were dissolved in trifluoroethanol (1 mL) andheated at reflux for 1 hour. To this was added 12 N HCl (3 mL) and the reaction allowed to heat at reflux for 2 hours. The product percipatated out upon cooling to room temperature, it was filtered off and washed with cold 2-propanol to give 3-chloropropyl 9-nitro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl sulfide (120 mg, 75.4%). 1H NMR (CD3OD, 300 MHz): δ8.00 (d, 1H, J=8.4 Hz), 7.30 (d, 1H, J=8.4 Hz), 4.68 (s, 2H), 3.69 (t, 2H, J=6.2 Hz), 3.60 (t, 2H, J=6 Hz), 3.23 (t, 2H, J=6.2 Hz), 2.08 (q, 2H, J=6.2 Hz) ppm.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureto heat
  3. temperatureat reflux for 2 hours
  4. filtrationit was filtered off
  5. washwashed with cold 2-propanol

Sources & evidence

ORD record
ord-1d67e5c2c3704b33860b3e4af6d177eb
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

Loading…