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Sodium Hydroxide → 1-(2-Chloro-3-methylphenyl)-4-(3,4,5-trimethoxybenzyl)piperazine

HRID 1738805
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HRID 1738805 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:24][CH2:23][N:22]([C:25]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=2)=O)[CH2:21][CH2:20]1.[OH-].[Na+]>C(OCC)C.O1CCCC1>[Cl:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:20][CH2:21][N:22]([CH2:25][C:27]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=2)[CH2:23][CH2:24]1
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반응물 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 15434661[4-(2-Chloro-3-methylphenyl)piperazine-1-yl]-(3,4,5-trimethoxyphenyl)methanoneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 102938041-(2-Chloro-3-methylphenyl)-4-(3,4,5-trimethoxybenzyl)piperazine수율 85.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of aluminum chloride (0.279 g, 2.09 mmol) in anhydrous diethyl ether (20 mL) is added dropwise to a suspension of lithium aluminum hydride (0.238 g, 6.27 mmol) in anhydrous tetrahydrofuran (20 mL) at 0° C. and stirred for 0.5 hour. To this mixture is added dropwise a solution of [4-(2-chloro-3-methylphenyl)piperazine-1-yl]-(3,4,5-trimethoxy-phenyl)methanone (2.12 g, 5.23 mmol) in anhydrous tetrahydrofuran (20 mL). The suspension is stirred for 2 hours at 0° C., followed by dropwise addition of 2N sodium hydroxide. The mixture is filtered through Celite and concentrated in vacuo. The resulting product is purified by MPLC on silica gel eluting with 40% ethyl acetate/hexane to give 1.74 g of the title compound as a white solid; mp 112-113° C.

후처리

  1. stirringThe suspension is stirred for 2 hours at 0° C.
  2. filtrationThe mixture is filtered through Celite
  3. concentrationconcentrated in vacuo
  4. customThe resulting product is purified by MPLC on silica gel eluting with 40% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-f0b67009c3ca46a29ac3c7874d219f19
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05965560

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