Hydrazine → 2-Hydrazinyl-5,6,7,8,9,10-hexahydrocyclooct[b]pyridine

HRID 452388

Reaction equation

HRID 452388 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:5]2=[CH:4][CH:3]=1.[NH2:14][NH2:15]>C(O)C>[NH:14]([C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:5]2=[CH:4][CH:3]=1)[NH2:15]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 581995322-Chloro-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Product 1

HCID 552819282-Hydrazinyl-5,6,7,8,9,10-hexahydrocyclooct[b]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
150 °C

Procedure

2-chloro-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine was treated with ethanol (20 mL) and anhydrous hydrazine (5 mL) in a sealed tube at 150° C. bath temperature for 7 h. Initial experiments showed that the addition did not proceed in boiling ethanol at atmospheric pressure. HPLC showed that the addition was incomplete, so the reaction mixture was heated at 150° C. for a further 7 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel, eluting with 95% dichloromethane and 5% of a 2M solution of ammonia in methanol; 1H NMR (CDCl3, 300 MHz) 7.19 (d, 1H), 6.51 (d, 1H), 5.85 (br s, 1H), 3.77 (br s, 2H), 2.79 (m, 2H), 2.63 (m, 2H), 1.73 (m, 2H), 1.62 (m, 2H), 1.36 (m, 4H) ppm; 13C NMR (CDCl3, 75 MHz) 156.87, 158.54, 138.81, 126.67, 104.58, 34.72, 32.67, 31.45, 30.85, 26.41, 26.37; MS (ES) 192 (M+H).

Workup

  1. additionInitial experiments showed that the addition
  2. additionHPLC showed that the addition
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel
  5. washeluting with 95% dichloromethane and 5% of a 2M solution of ammonia in methanol

Sources & evidence

ORD record
ord-4babd4090a13468b9b4767832da2b11a
Source dataset
uspto-grants-2013_07
Patent number
US08492373B2

Linked notes

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