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Diisopropylethylamine → 6-[6-(Allyl-methyl-amino)-hexyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester

HRID 49483
ノート
印刷プレビュー

反応式

HRID 49483 の反応式
[CH2:1]([N:4]([CH3:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH2:17][CH2:16][CH2:15]2)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)=[O:34]>C(Cl)Cl>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([O:35][C:33]([N:18]2[C:19]3[C:14](=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH:2]=[CH2:3])[CH3:22])=[CH:21][CH:20]=3)[CH2:15][CH2:16][CH2:17]2)=[O:34])=[CH:37][CH:38]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 21966553Allyl-methyl-[6-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-hexyl]-amine

生成物 1

HCID 695147796-[6-(Allyl-methyl-amino)-hexyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester収率 50.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane
触媒
HCID 6344Dichloromethane溶媒

実験手順

To 60.4 mg (0.2 mmol) Allyl-methyl-[6-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-hexyl]-amine in 2 ml CH2Cl2 1 drop of Huenig's base and 57 mg (0.3 mmol) 4-chlorophenyl chloroformate in 1 ml CH2Cl2 were added. The solution was stirred at RT for 30 min, was concentrated and the residue was dissolved in ether and a saturated aqueous solution of NaHCO3. The inorganic phase was extracted with ether and the combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1 yielded 46 mg (50%) 6-[6-(Allyl-methyl-amino)-hexyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester as colorless oil, MS: 457 (MH+, 1Cl).

後処理

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in ether
  3. extractionThe inorganic phase was extracted with ether
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-19aebbc61a9b4725be1830a1627da180
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06706751B2

反応ノート

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