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

HRID 1896270노트

반응식

HRID 1896270 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 9533Bis(2-chloroethyl)amineHCID 12370795HCID 12370795, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c7ea67d264d417db8234e9a5046e4fe
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518948B2

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