Hydrochloric Acid → Diethyl 2-(4-(piperazin-1-yl)benzyl)-2-methylmalonate

HRID 1896275노트

반응식

HRID 1896275 반응식
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]([CH3:18])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]Cl.Cl>C1(C)C(C)=CC=CC=1>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([CH2:6][C:7]([CH3:18])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:19][CH:20]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 9533Bis(2-chloroethyl)amineHCID 54055855Diethyl methyl-(4-amino)benzylmalonate

생성물 1

HCID 67382829Diethyl 2-(4-(piperazin-1-yl)benzyl)-2-methylmalonate수율 76.3%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A solution of diethyl 2-(4-aminobenzyl)-2-methylmalonate (2.00 g, 7.17 mmol) and Bis-(2-chloroethyl) amine.HCl (1.90 g, 10.8 mmol) in xylene (10 ml) were heated at reflux for 48 h. The reaction mixture was concentrated and the residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The separated organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product. Purification by column chromatography over neutral alumina using 5% methanol in CHCl3 as eluent afforded 1.90 g (76.3%) of diethyl 2-(4-(piperazin-1-yl)benzyl)-2-methylmalonate as brown oil.

후처리

  1. temperatureat reflux for 48 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  4. washThe separated organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customPurification by column chromatography over neutral alumina using 5% methanol in CHCl3 as eluent

출처 및 근거

ORD 기록
ord-911eed60660345f2817c2aeec12b8d19
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518948B2

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