1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin

HRID 37164

반응식

HRID 37164 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.OC1C2N=NNC=2C=CC=1.[OH:43][C:44]1[CH:56]=[CH:55][C:47]2[O:48][C:49]([C:52](O)=[O:53])=[CH:50][O:51][C:46]=2[CH:45]=1>CN(C)C=O>[OH:43][C:44]1[CH:56]=[CH:55][C:47]2[O:48][C:49]([C:52]([N:12]3[CH2:11][CH2:10][N:9]([CH:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)[CH2:14][CH2:13]3)=[O:53])=[CH:50][O:51][C:46]=2[CH:45]=1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 110632916-Hydroxy-1,4-benzodioxin-2-carboxylic acidHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 98044716-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Under a nitrogen atmosphere, add 5.5 mmol of 1-[bis(4-fluorophenyl)methyl]piperazine, 5.5 mmol of EDCI (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide) and 5.5 mmol of HOBt (hydroxybenzotriazole) in succession to a solution at 0° C. of 5 nmml of 6-hydroxy-1,4-benzodioxin -2-carboxylic acid in 25 cm3 of N,N-dimethylformamide. Stir for 2 hours at 0° C. and then for 12 hours at room temperature, and concentrate the reaction mixture under reduced pressure. Extract the resulting amide with diethyl ether and then, after concentration to dryness, purify the crude product by chromatography on a silica column (eluant:petroleum ether then an increasing gradient of ethyl acetate in petroleum ether). 6-Hydroxy-2-{4-[bis-(4-fluorophenyl)methyl]piperazin-1-ylcarbonyl}-1,4-benzodioxin is thereby obtained in a yield of 85%. The product obtained is precipitated from 10 ml of pentane and is then filtered and recrystallised from cyclohexane.

후처리

  1. waitfor 12 hours at room temperature
  2. concentrationconcentrate the reaction mixture under reduced pressure
  3. extractionExtract the resulting amide with diethyl ether
  4. concentrationafter concentration to dryness
  5. custompurify the crude product by chromatography on a silica column (eluant

출처 및 근거

ORD 기록
ord-da61facdfcae4470a9b632686e8809ea
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420132

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