Trifluoroacetic acid → 5-Methyl-7-piperidino-1H-pyrazolo(4,3-b)pyridine

HRID 637980Notes

Reaction equation

HRID 637980 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.[C:12](O)([C:14](F)(F)F)=O>N1CCCCC1>[CH3:8][C:6]1[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]2=[C:2]([N:5]2[CH2:14][CH2:12][CH2:2][CH2:3][CH2:4]2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 116798717-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 202548665-Methyl-7-piperidino-1H-pyrazolo(4,3-b)pyridine

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

7-Chloro-5-methyl-1H-pyrazolo(4,3-b)pyridine (1 g) and piperidine (10 ml) were heated under reflux for 24 h. The piperidine was removed in vacuo to yield a pale yellow solid which was washed with water to yield the piperidino-compound (1 g, 78%), Crystallisation from ethanol-water gave pale yellow crystals, m.p. 244°. Found: C, 66.5; H, 7.55.; N, 25.7. C12H16N4 requires C, 66.6; H, 7.5; N, 25.9%), νmax 2660-2200 (broad), 2000-1800 (broad), 1540, 1430, 1355, 1290, 1210, 1020, 980, 810 and 760 cm-1, δ (CF3COOH) 1.97 (6H, s, --CH2 --), 2.70 (3H, s, 5 --CH3), 4.13 (4H, s, --N--CH2 --), 6.59 (1H, s, 6-H), 8.32 (1H, s, 3-H), total proton count 15.

Workup

  1. temperatureunder reflux for 24 h
  2. customThe piperidine was removed in vacuo
  3. customto yield a pale yellow solid which
  4. washwas washed with water
  5. customto yield
  6. customthe piperidino-compound (1 g, 78%), Crystallisation from ethanol-water
  7. customgave pale yellow crystals, m.p. 244°

Sources & evidence

ORD record
ord-7ff64210370c4957af3dfa31a417b3cc
Source dataset
uspto-grants-1985_12
Patent number
US04559348

Reaction notes

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