Bromomethylcyclopropane → (4-Bromo-phenyl)-[4-[6-(cyclopropylmethyl-methyl-amino)-hexyloxy]-phenyl]-methanone

HRID 1636745ノート

反応式

HRID 1636745 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH3:24])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:35][CH:36]1[CH2:38][CH2:37]1>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:35][CH:36]3[CH2:38][CH2:37]3)[CH3:24])=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 81503BromomethylcyclopropaneHCID 81531DiisopropylethylamineHCID 10905217HCID 10905217、化合物

生成物 1

HCID 11059310(4-Bromo-phenyl)-[4-[6-(cyclopropylmethyl-methyl-amino)-hexyloxy]-phenyl]-methanone

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 0.1 g of (4-bromo-phenyl)-[4-(6-methylamino-hexyloxy)-phenyl]-methanone, 0.13 ml of diisopropylethylamine and 0.06 ml of bromomethyl-cyclopropane in 20 ml of dimethyl-acetamide is stirred at 50° C. for 24 hrs., concentrated and the residue is treated with sodium hydrogen carbonate solution and extracted with methylene chloride. The organic phases are washed with saturated sodium chloride solution, dried and evaporated. The residue is purified over silica gel with CH2Cl2 /MeOH/NH4OH (94/5.410.6 to 85/12.5/2.5). There is obtained 0.68 g of (4-bromo-phenyl)-[4-[6-(cyclopropylmethyl-methyl-amino)-hexyloxy]-phenyl]-methanone which is converted into the fumarate, MS: m/e 443 (M+H+, 1Br).

後処理

  1. concentration, concentrated
  2. additionthe residue is treated with sodium hydrogen carbonate solution
  3. extractionextracted with methylene chloride
  4. washThe organic phases are washed with saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customThe residue is purified over silica gel with CH2Cl2 /MeOH/NH4OH (94/5.410.6 to 85/12.5/2.5)

出典と根拠

ORDレコード
ord-ea5080be4d344d63b70fc93e14fff1b6
出典データセット
uspto-grants-2000_03
特許番号
US06034275

反応ノート

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