N-Methylallylamine → 6-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 49478

反応式

HRID 49478 の反応式
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][CH2:22]Br)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH:27][CH3:28])[CH:25]=[CH2:26]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:27]([CH2:24][CH:25]=[CH2:26])[CH3:28])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 69391N-MethylallylamineHCID 695151816-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

生成物 1

HCID 695154176-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5.0 g (13.0 mmol) 6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester were treated with 3.66 g (51.5 mmol) N-allyl-methylamine in 100 ml DMF at 50° C. for 30 min. The mixture was concentrated in vacuo, dissolved in Et2O and water. The inorganic layer was extracted with Et2O, and the combined organic phases were washed with water and dried over Na2SO4. Purification by column chromatography on silica gel with CH2Cl2/MeOH 10:1 yielded 3.6 g (74%) 6-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as light yellow oil, MS: 375 (MH+).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in Et2O
  3. extractionThe inorganic layer was extracted with Et2O
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customPurification by column chromatography on silica gel with CH2Cl2/MeOH 10:1

出典と根拠

ORDレコード
ord-6b8b37ce99ad41bdb69ce4f9f30ee8ef
出典データセット
uspto-grants-2004_03
特許番号
US06706751B2

関連ノート

読み込み中…