Reaction #79240

Reaction equation

1-{2-[(3-Chloropropyl)sulfanyl]-5-nitrophenyl}hydrazine

4-piperidone mono hydrate

HCl

→

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

Yield 96.9%

Solvents

trifluoroethanol

Conditions

Workup

1. 1
   Temperatureat reflux for 1 hour
2. 2
   Temperatureto heat
3. 3
   Temperatureat reflux for 2 hours
4. 4
   Filtrationit was filtered off
5. 5
   Washwashed with cold 2-propanol

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.

Source