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

HRID 2306486노트

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HRID 2306486 반응식
[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

참가 물질

5

반응물 3

HCID 81503BromomethylcyclopropaneHCID 81531DiisopropylethylamineHCID 10905217HCID 10905217, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
50 °C

실험 절차

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 dimethylacetamide 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 (9415.410.6 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).

후처리

  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 (9415.410.6 to 85/12.5/2.5)

출처 및 근거

ORD 기록
ord-19df42fa03044e71801f5640e3781fcd
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06441177B1

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