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

HRID 452388

반응식

HRID 452388 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4babd4090a13468b9b4767832da2b11a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492373B2

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