Propanolamine ethyl ether → N-Anthracen-9-ylmethyl-N'-(3-ethoxy-propyl)-N-ethyl-propane-1,3-diamine

HRID 12996

反応式

HRID 12996 の反応式
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19]OS(C)(=O)=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH2:27]([O:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH3:28]>C(#N)C>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19][NH:33][CH2:32][CH2:31][CH2:30][O:29][CH2:27][CH3:28])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 22720Propanolamine ethyl etherHCID 86615041Methanesulfonic acid 3-(anthracen-9-ylmethyl-ethyl-amino)-propyl ester

生成物 1

HCID 24744196N-Anthracen-9-ylmethyl-N'-(3-ethoxy-propyl)-N-ethyl-propane-1,3-diamine収率 60%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
75 °C

実験手順

The mesylate 17 (584 mg, 1.57 mmol) and 3-ethoxypropylamine (649 mg, 6.30 mmol) were dissolved in acetonitrile (30 mL). The mixture was then stirred at 75° C. under a N2 atmosphere overnight. After the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (25 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 19 as a light yellow oil. Yield 60%; Rf=0.35 (0.5:4:85.5 NH4OH:MeOH:CH2Cl2); 1H NMR (CDCl3) δ 8.43 (d, 2H), 8.29 (s, 1H), 7.89 (d, 2H), 7.40 (m, 4H), 4.38 (s, 2H), 3.35 (q, 2H), 3.25 (t, 2H), 2.62 (q, 2H), 2.44 (t, 2H), 2.27 (t, 2H), 2.23 (t, 2H), 1.54 (q, 2H), 1.41 (q, 2H), 1.14 (m, 6H); 13C NMR (CDCl3) δ 131.3, 131.2, 130.6, 128.9, 127.2, 125.4, 125.0, 124.7, 69.1, 66.0, 50.7, 50.6, 48.2, 47.5, 47.2, 30.1, 27.1, 15.4, 11.9.

後処理

  1. concentrationAfter the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (25 mL)
  3. washwashed three times with aqueous sodium carbonate
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-90a9e413fceb40e598299cf0c7f7ac3f
出典データセット
uspto-grants-2010_06
特許番号
US07728041B2

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