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

HRID 2406136

反応式

HRID 2406136 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7c395deb5c66452e8bf3ccdcf8d1a12d
出典データセット
uspto-grants-2014_08
特許番号
US08809347B2

関連ノート

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