Tetrahydrofuran → (1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-benzylpiperidin-4-yl)amine

HRID 323180

反応式

HRID 323180 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1.[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(OCCCl)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N(CC)CC)C.O>[CH2:25]([O:24][CH2:28][CH2:27][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)[CH3:26]

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 12341Ethane, 1-chloro-2-ethoxy-2 回HCID 3251421Potassium bis(trimethylsilyl)amideHCID 16640950N-(1-Benzylpiperidin-4-yl)-1H-benzimidazol-2-amine

生成物 1

HCID 13808349(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-benzylpiperidin-4-yl)amine

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 8471Triethylamine溶媒

反応条件

温度
-78 °C

実験手順

Combine (1H-benzimidazol-2-yl)(1-benzylpiperidin-4-yl)amine (0.5 g, 1.6 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. Add dropwise, a solution of potassium bis(trimethylsilyl)amide (3.6 mL, 0.5 M in toluene, 1.8 mmol). After 30 minutes, add 2-chloroethyl ethyl ether (0.2 g, 1.8 mmol). Warm to ambient temperature and heat to reflux. After 4 hours, add 2-chloroethyl ethyl ether (0.2 g, 1.8 mmol) and tetrabutylammonium bromide (0.1 g). After 12 hours, cool to ambient temperature and add water. Separate the organic layer and extract the aqueous layer with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2% triethylamine/10% methanol/ethyl acetate to give (1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-benzylpiperidin-4-yl)amine: Rf=0.55 (2% triethylamine/10% methanol/ethyl acetate).

後処理

  1. additionAdd dropwise
  2. temperatureWarm to ambient temperature
  3. temperatureheat to reflux
  4. waitAfter 4 hours
  5. waitAfter 12 hours
  6. temperaturecool to ambient temperature
  7. customSeparate the organic layer
  8. extractionextract the aqueous layer with dichloromethane
  9. dry with materialDry the combined organic layers over Na2SO4
  10. filtrationfilter
  11. customevaporate in vacuo
  12. customto give a residue

出典と根拠

ORDレコード
ord-20895114483c47f899ae3cbfcfa8a476
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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