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

HRID 353628

反応式

HRID 353628 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-f65b6adc4d0848f6ad1b0bda1598dcb6
出典データセット
uspto-grants-2004_06
特許番号
US06753322B2

関連ノート

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