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

HRID 1756034

反応式

HRID 1756034 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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 mmol 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. Melting point: 163° C. ##STR58##

後処理

  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

出典と根拠

ORDレコード
ord-349adeeb984d4e7fbadc3b919174fba6
出典データセット
uspto-grants-1995_08
特許番号
US05439909

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