Triethylamine → Emedastine

HRID 637016노트

반응식

HRID 637016 반응식
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

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 2283491-Methylhomopiperazine2회HCID 104893562-chloro-1-(2-ethoxyethyl)-1H-benzimidazoleHCID 21226206Ethyl acetate hexane

생성물 1

HCID 3219Emedastine

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a4d5baae8064d5aac0a7606d59f1d28
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194406B1

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