Hydrochloric Acid → 6-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

HRID 911207ノート

反応式

HRID 911207 の反応式
[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[ClH:14].CCCCCCC>C(O)C>[ClH:14].[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 8900HeptaneHCID 138533586-Methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

生成物 1

HCID 574580206-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride収率 63%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Dissolve crude 6-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (35.1 g, 0.198 mol) in 2B-3 ethanol (250 mL), heat the solution to reflux and add 2M HCl in ethanol (108.9 mL, 0.218 mol, 1.1 equiv.). Slowly add heptane (700 mL) over 10 min, then remove the heating mantle and cool the solution to ambient temperature, and finally continue the cooling with an ice/water mixture. Collect the resulting solid by vacuum filtration and wash with cold ethanol:heptane (1:2) (3×100 mL), air-dry for 15 min under vacuum, then further dry the product in a vacuum oven at 60° C. for 1 h to give the desired intermediate as a white granular solid (35.53 g, 63%): mp 246.6-246.9° C.; 1H NMR (300 MHz, DMSO-d6), δ 9.82 (broad s, 1H), 7.12 (dd, 1H, J=7.6, 7.9), 6.88 (d, 1H J=8.2), 6.78 (d, 1H, J=7.3), 3.75 (s, 3H), 3.20-3.00 (m, 8H); 13C NMR (300 MHz, DMSO-d6), δ 156.2, 141.3, 127.4, 127.2, 121.6, 109.7, 55.7, 44.9, 44.7, 31.6, 21.7; MS (ES+) m/z 178 (M+H)+; Anal. Calc'd for C11H15ClNO: C, 62.12; H, 7.11; N, 6.59. Found: C, 61.95; H, 7.64; N, 6.58.

後処理

  1. temperatureheat the solution
  2. temperatureto reflux
  3. customremove the heating mantle
  4. customCollect the resulting solid
  5. filtrationby vacuum filtration
  6. washwash with cold ethanol:heptane (1:2) (3×100 mL)
  7. customair-dry for 15 min under vacuum
  8. customfurther dry the product in a vacuum oven at 60° C. for 1 h

出典と根拠

ORDレコード
ord-d45e3a401c5a4015bf413473694a5b86
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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