Potassium Carbonate → 6-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 49475

反応式

HRID 49475 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][CH2:23]Br)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([NH:28][CH3:29])[CH:26]=[CH2:27].C([O-])([O-])=O.[K+].[K+]>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][CH2:23][N:28]([CH2:25][CH:26]=[CH2:27])[CH3:29])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 69391N-MethylallylamineHCID 695149026-(5-Bromo-pentyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

生成物 1

HCID 695146996-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester収率 72.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.5 g (3.75 mmol) 6-(5-Bromo-pentyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester were treated with 355 mg (5 mmol) N-allyl-methylamine and 830 mg (6 mmol) K2CO3 (powdered) in 8 ml DMF at 60° C. for 3 h. The mixture was concentrated in vacuo, dissolved in acetone and filtered. The filtrate was concentrated and purified by column chromatography on silica gel with CH2Cl2/MeOH 19:1 to yield 1.05 g (72%) 6-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as colorless oil, MS: 389 (MH+).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in acetone
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography on silica gel with CH2Cl2/MeOH 19:1

出典と根拠

ORDレコード
ord-61cd16c352fa472590d986d03d2eee59
出典データセット
uspto-grants-2004_03
特許番号
US06706751B2

関連ノート

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