Dimethylamine → 1-[4-[[4-[2-[3-(Dimethylamino)propyl]-2H-tetrazol-5-yl]phenoxy]methyl]-2-hydroxy-3-propylphenyl]ethanone

HRID 620242ノート

反応式

HRID 620242 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[N:20][N:21]([CH2:23][CH2:24][CH2:25]Br)[N:22]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[CH3:31][NH:32][CH3:33]>C(#N)C>[CH3:31][N:32]([CH3:33])[CH2:25][CH2:24][CH2:23][N:21]1[N:20]=[N:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:7]3[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[C:5]([OH:30])[C:6]=3[CH2:27][CH2:28][CH3:29])=[CH:13][CH:14]=2)=[N:22]1

参加物

4

反応物 2

HCID 674DimethylamineHCID 144581835-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)]-2-(3-bromopropyl)-2H-tetrazole

生成物 1

HCID 144582091-[4-[[4-[2-[3-(Dimethylamino)propyl]-2H-tetrazol-5-yl]phenoxy]methyl]-2-hydroxy-3-propylphenyl]ethanone収率 88.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

5-[4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl]-2-(3-bromopropyl)-2H-tetrazole (2.8 g, 0.006 mol) was dissolved in acetonitrile and cooled to 10 approximately 0° C. Dimethylamine (anhydrous, excess) was cooled in the reagent bottle before it was opened then added to the cool acetonitrile solution. The solution was maintained at approximately 0° C. with an ice bath while it was stirred (approximately 5 hours). The reaction mixture was then concentrated in vacuo. Water was added and the resultant solution was extracted with ethyl acetate. The ethyl acetate layers were combined, washed with water and dried over sodium sulfate. The dried ethyl acetate layers were concentrated and the resultant residue was chromatographed by HPLC (preparatoryscale, silica gel column, eluted isocratically with a mixture of 9.5 : 0.5 methylene chloride:methanol to which 0.05% of diethylamine had been added to yield 2.3 g, 88.5% yield of the title product: m.p. 89°-91° C.; n.m.r.: (300 MHz, CDCl3) δ: 1.0 (t, 2H); 1.6 (m, 2H); 2.1 (t, 2H); 2.2 (s, 6H); 2.3, (t, 2H); 2.4 (t, 2H); 2.6 (s, 3H); 2.7 (t, 2H); 4.7 (t, 2H); 5.2 (s, 2H); 7.1 (2d, 3H); 7.6 (d, 1H); 8.1 (d, 2H); 12.7 (s, 1H).

後処理

  1. temperatureThe solution was maintained at approximately 0° C. with an ice bath while it
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additionWater was added
  4. extractionthe resultant solution was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe dried ethyl acetate layers were concentrated
  8. customthe resultant residue was chromatographed by HPLC (preparatoryscale, silica gel column
  9. washeluted isocratically with a mixture of 9.5 : 0.5 methylene chloride
  10. additionmethanol to which 0.05% of diethylamine had been added

出典と根拠

ORDレコード
ord-5c9952f878c14f299c89d7be74702718
出典データセット
uspto-grants-1989_04
特許番号
US04820722

反応ノート

読み込み中…