Formaldehyde → 1,2,3,4-Tetrahydro[1]benzothieno[2,3-c]pyridine

HRID 501210

反応式

HRID 501210 の反応式
Cl.[S:2]1[CH:6]=[C:5]([CH2:7][CH2:8][NH2:9])[C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2.[CH2:14]=O>CO>[CH2:14]1[C:6]2[S:2][C:3]3[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=3[C:5]=2[CH2:7][CH2:8][NH:9]1

参加物

4

反応物 2

HCID 712FormaldehydeHCID 209554Benzo(b)thiophene-3-ethylamine, hydrochloride

生成物 1

HCID 4132821,2,3,4-Tetrahydro[1]benzothieno[2,3-c]pyridine収率 36.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 2-(benzo[b]thien-3-yl)ethylamine hydrochloride (0.5 g, 2.34 mmol) and paraformaldehyde (0.125 g, 4.16 mmol) in methanol (15 mL) was refluxed for 24 h. The reaction mixture was concentrated under reduce pressure and the residue was neutralized with saturated NaHCO3 (50 mL), and extracted with ethyl acetate (2×50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to furnish 1,2,3,4-tetrahydro[1]benzothieno[2,3-c]pyridine (160 mg, 35%); 1H NMR (200 MHz, CDCl3): δ 2.81 (m, 2H), 3.25 (m, 2H), 4.15 (s,2H), 7.30 (m, 2H), 7.69 (d, J=4.0 Hz, 1H), 7.79 ((d, J=4.0 Hz, 1H).

後処理

  1. temperaturewas refluxed for 24 h
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-4ae6b99d74d845389947fddfde6d1c34
出典データセット
uspto-grants-2010_08
特許番号
US07772245B2

関連ノート

読み込み中…