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

HRID 501210

반응식

HRID 501210 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4ae6b99d74d845389947fddfde6d1c34
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772245B2

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