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

HRID 1896275ノート

反応式

HRID 1896275 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-911eed60660345f2817c2aeec12b8d19
出典データセット
uspto-grants-2013_08
特許番号
US08518948B2

反応ノート

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