Hydrochloric Acid → Formic acid N'-[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethyl]-hydrazide, dihydrochloride

HRID 507381ノート

反応式

HRID 507381 の反応式
[ClH:1].[CH3:2][N:3]([CH3:20])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][NH:16][NH:17][CH:18]=[O:19])[CH:13]=2)[NH:8][CH:7]=1>CCOCC.C1COCC1>[ClH:1].[ClH:1].[CH3:20][N:3]([CH3:2])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][NH:16][NH:17][CH:18]=[O:19])[CH:13]=2)[NH:8][CH:7]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 11565615formic acid N'-[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethyl]-hydrazide

生成物 1

HCID 131728313Formic acid N'-[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethyl]-hydrazide, dihydrochloride

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of HCl in ether (49.1 ml of a 2.138 molar solution, 105 mmol) is added under a nitrogen atmosphere to a solution of formic acid N′-[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethyl]-hydrazide (Example 13; 26.03 g, 100 mmol) in THF (300 ml) within 10 minutes. The obtained thick suspension of the product is filtered, and the filter cake washed with THF (ca. 80 ml) and ether (ca. 100 ml). The product is dried over night to give 28.04 g (84%) of cream colored hygroscopic crystals. 1H-NMR (DMSO-D6, 300 Mhz) □ 2.81 (s, 6H, HN+(CH3)2); 3.13 (m, 2H, CH2); 3.30 (m, 2H, CH2); 4.05 (s, 2H, CH2N+); 7.10 (dd, 1H, J=8.3 Hz, J=1.7 Hz, H-6); 7.21 (d, J=2.6 Hz, H-2); 7.32 (d, 1H, H-7); 7.63 (d, 1H, H-4); 7.96 (s, 1H, CHO); 10.9-11.15 (brs, H+); 11.10 (d, 1H, NH).

後処理

  1. additionThe obtained thick suspension of the product
  2. filtrationis filtered
  3. washthe filter cake washed with THF (ca. 80 ml) and ether (ca. 100 ml)
  4. customThe product is dried over night
  5. customto give 28.04 g (84%) of cream

出典と根拠

ORDレコード
ord-7e13a81963e44bfd9a604ad40308422d
出典データセット
uspto-grants-2010_08
特許番号
US07786156B2

反応ノート

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