Methanol → 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-1-(methoxymethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1971032

反応式

HRID 1971032 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26](=[O:32])[N:27]3[CH2:30][OH:31])=[CH:22][CH:21]=2)[CH2:11][CH2:10]1.S(Cl)(Cl)=O.CO.[C:39]([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26](=[O:32])[N:27]3[CH2:30][O:31][CH3:39])=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 58096483N-Hydroxymethyl aripiprazole

生成物 1

HCID 580967487-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-1-(methoxymethyl)-3,4-dihydroquinolin-2(1H)-one収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of hemiaminal A1 (2.0 g, 4.2 mmol) in dichloromethane (20 mL) was added thionyl chloride (1.5 mL, 12.6 mmol) and stirred for 2 h at room temperature. To the reaction mixture was added methanol (10 mL) and stirred a further 2 h. The reaction poured into NaHCO3 (aq) and extracted with dichloromethane. The organic phase dried over MgSO4, evaporated and the residue purified on silica eluting with 1:1:0.1 dichloromethane/ethyl acetate/methanol to give the title compound as a cream solid (1.3 g, 63%).

後処理

  1. stirringstirred a further 2 h
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase dried over MgSO4
  4. customevaporated
  5. customthe residue purified on silica eluting with 1:1:0.1 dichloromethane/ethyl acetate/methanol

出典と根拠

ORDレコード
ord-5a05b82a700542d584650fd66e048c21
出典データセット
uspto-grants-2013_04
特許番号
US08431576B2

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