Diethyl Ether → N-[3-(3-piperidinomethylphenoxy)propyl]phthalimide

HRID 1609459

반응식

HRID 1609459 반응식
[H-].[Na+].[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].C(OCC)C>CN(C)C=O.O>[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[O:16][CH2:18][CH2:19][CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 8269741-(3-Hydroxybenzyl)piperidine

생성물 1

HCID 12898565N-[3-(3-piperidinomethylphenoxy)propyl]phthalimide수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

실험 절차

In an argon stream, 2.2 g of 60% sodium hydride was suspended in 20 ml of N,N-dimethylformamide. The suspension was added dropwise to a solution of 9.6 g of the 3-(1-piperidinomethyl)phenol obtained in Reference Example 1 in 30 ml of N,N-dimethylformamide, followed by stirring at room temperature for 30 minutes. Next, a solution of 14.7 g of N-(3-bromopropyl)phthalimide in 50 ml of N,N-dimethylformamide was added dropwise to the mixture, and the resulting mixture was stirred at 65° C. for 8 hours. After cooling the mixture, a mixture of diethyl ether and water (1:1) was added thereto for extraction, and the organic layer was concentrated under reduced pressure. To the concentrate was added 6N hydrochloric acid for extraction into the aqueous layer, which was then made alkaline with potassium hydroxide, followed by extraction with diethyl ether. The organic layer was dried over magnesium sulfate and distilled under reduced pressure to remove the solvent, giving 16.3 g of transparent oily N-[3-[3-(piperidinomethyl)-phenoxy]propyl]phthalimide (yield 86% ).

후처리

  1. stirringthe resulting mixture was stirred at 65° C. for 8 hours
  2. temperatureAfter cooling the mixture
  3. additionwas added
  4. extractionfor extraction
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. additionTo the concentrate was added 6N hydrochloric acid
  7. extractionfor extraction into the aqueous layer, which
  8. extractionfollowed by extraction with diethyl ether
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent

출처 및 근거

ORD 기록
ord-ea2612bbb173493b8c43f0d4b909199d
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05401739

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