Hydrochloric Acid → Diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonate

HRID 1896270ノート

反応式

HRID 1896270 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Cl[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]Cl.Cl>C1(C)C(C)=CC=CC=1>[CH3:19][C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:1]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:3][CH:4]=1)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 9533Bis(2-chloroethyl)amineHCID 12370795HCID 12370795、化合物

生成物 1

HCID 67382666Diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonate収率 63.5%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A suspension of diethyl 2-(4-aminophenyl)-2-methylmalonate (6.00 g, 22.6 mmol), Bis-(2-chloroethyl) amine.HCl (4.82 g, 27.2 mmol) in xylene (20 ml) was refluxed for 48 h. The reaction mixture was concentrated in vacuo 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 under reduced pressure to afford crude product. Purification by column chromatography over neutral alumina using 5% MeOH in CHCl3 as eluent afford 4.80 g (63.5%) of diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonate as brown oil.

後処理

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

出典と根拠

ORDレコード
ord-1c7ea67d264d417db8234e9a5046e4fe
出典データセット
uspto-grants-2013_08
特許番号
US08518948B2

反応ノート

読み込み中…