Triethylamine → Emedastine

HRID 1584426

反応式

HRID 1584426 の反応式
Cl[C:2]1[N:6]([CH2:7][CH2:8][O:9][CH2:10][CH3:11])[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[N:3]=1.[CH3:16][N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)CC)C.C(OCC)(=O)C.CCCCCC>CO.ClCCl>[CH3:16][N:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:2]2[N:6]([CH2:7][CH2:8][O:9][CH2:10][CH3:11])[C:5]3[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=3[N:3]=2)[CH2:19][CH2:18]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2283491-Methylhomopiperazine2 回HCID 104893562-chloro-1-(2-ethoxyethyl)-1H-benzimidazoleHCID 21226206Ethyl acetate hexane

生成物 1

HCID 3219Emedastine

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
70 °C

実験手順

Combine 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole (22.3 g, 99.4 mmol), 1-methyl[1,4]diazepane (19 mL, 152.8 mmol), and triethylamine (75 mL). Heat to 70° C. After 18 hours, add 1-methyl[1,4]diazepane (10 mL) and continue to heat at reflux. After 96 hours, cool to ambient temperature and partition the reaction mixture between water and ethyl acetate. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 50% ethyl acetate/hexane and then 10% methanol/dichloromethane to give 1-methyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf =0.52 (silica gel, dichloromethane/methanol/concentrated aqueous ammonia, 90/10/0.1).

後処理

  1. temperatureto heat
  2. temperatureat reflux
  3. waitAfter 96 hours
  4. temperaturecool to ambient temperature
  5. custompartition the reaction mixture between water and ethyl acetate
  6. customSeparate the layers
  7. extractionextract the organic layer with a saturated aqueous sodium bicarbonate solution
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

出典と根拠

ORDレコード
ord-d5c0d523e05444fea8131e5e32a05775
出典データセット
uspto-grants-1999_08
特許番号
US05932571

関連ノート

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