1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 2-[2-(4-isopropyl-1-piperidinyl)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 10447

反応式

HRID 10447 の反応式
[CH:1]([CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].Br[CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]([CH:4]1[CH2:9][CH2:8][N:7]([CH2:11][CH2:12][N:13]2[C:14](=[O:23])[C:15]3[C:16](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:18])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 140569Piperidine, 4-(1-methylethyl)-

生成物 1

HCID 219782572-[2-(4-isopropyl-1-piperidinyl)ethyl]-1H-isoindole-1,3(2H)-dione収率 54.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 4-isopropylpiperidine (3.3 g, 20.2 mmol), N-(2-bromoethyl)phthalimide (5.4 g, 21.3 mmol), potassium carbonate (5.9 g, 45.4 mmol) and acetonitrile (100 ml) and was heated under reflux for 2.5 hours then stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was separated and the aqueous layer extracted with further ethyl acetate (100 ml). The combined organic extracts were dried (Na2SO4) and the solvent removed by evaporation under reduced pressure. The resulting oil was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane changing to dichloromethane:diethyl ether (50:50, by volume) changing to diethyl ether to afford the title compound (3.3 g).

後処理

  1. temperatureunder reflux for 2.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with further ethyl acetate (100 ml)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customthe solvent removed by evaporation under reduced pressure
  8. customThe resulting oil was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane changing to dichloromethane:diethyl ether (50:50, by volume)

出典と根拠

ORDレコード
ord-7efd89374aa24ed08aa7d37e2d91e9b1
出典データセット
uspto-grants-2006_08
特許番号
US07094769B2

関連ノート

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