Aluminium lithium hydride → 1-(Benzo[b]thiophen-2-yl)-N-methylmethanamine

HRID 1761097

반응식

HRID 1761097 반응식
[CH3:1][NH:2][C:3]([C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][CH2:3][C:5]1[S:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 22593821HCID 22593821, 화합물

생성물 1

HCID 6931411-(Benzo[b]thiophen-2-yl)-N-methylmethanamine수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a stirred suspension of N-methyl benzothiophene-2-carboxamide (10.0 g, 52 mmole) in dry THF (75 nL) under argon was added a solution of 1.0 M LiAlH4 in THF (135 mL, 135 mmole) over 15 minutes. The reaction quickly became clear and was heated at reflux for 2 days. After cooling to 0° C. the reaction was carefully quenched with the sequential addition of H2O (5.1 mL), 15% NaOH in H2O (5.I mL), and H2O (15.3 mL). The mixture was filtered through a pad of celite® and the filter pad was rinsed with Et2O (50 mL). The filtrate was concentrated to afford the title compound (9.11 g, 99%) as a pale yellow oil which solidified in the freezer: 1H NMR (400 MHz, CDCl3) δ 7.83 (d. J=7.3 Hz,1H), 7.72 (d, J=7.3 Hz. 1 H), 7.33 (m, 2H), 7.17 (s,1H), 4.06 (s, 2H), 2.53 (s, 3 H), 1.56 (br s,1H).

후처리

  1. customThe reaction quickly became clear
  2. temperaturewas heated
  3. temperatureat reflux for 2 days
  4. customwas carefully quenched with the sequential addition of H2O (5.1 mL), 15% NaOH in H2O (5.I mL), and H2O (15.3 mL)
  5. filtrationThe mixture was filtered through a pad of celite®
  6. washthe filter pad was rinsed with Et2O (50 mL)
  7. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-72214a184441438d8f03c917622e2e64
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06846819B1

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