Hydrochloric Acid → 1,1-Dimethylethyl 4-[(5-amino-2-chlorophenyl)methyl]-1-piperazinecarboxylate

HRID 1750883노트

반응식

HRID 1750883 반응식
Cl.[Cl:2][C:3]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1>[Fe].C(O)C.O>[NH2:23][C:20]1[CH:21]=[CH:22][C:3]([Cl:2])=[C:4]([CH:19]=1)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:8][CH2:7]1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 57678518HCID 57678518, 화합물

생성물 1

HCID 576785351,1-Dimethylethyl 4-[(5-amino-2-chlorophenyl)methyl]-1-piperazinecarboxylate수율 86.2%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 19096565Water ethanol용매

실험 절차

Iron (1.7 g, 26.7 mmol) and concentrated hydrochloric acid (0.2 mL) were added to ethanol/water (45 mL/45 mL), and refluxed for 1 hour. The mixed reaction solution was added with tert-butyl 4-(2-chloro-5-nitrobenzyl)piperazine-1-carboxylate (1.9 g, 5.34 mmol) obtained in <Step 1> above, and further refluxed for 1 hour. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with ethanol and chloroform/2-propanol=3/1 (v/v). The resulting filtrate was distilled under reduced pressure and dissolved in ethanol and chloroform/2-propanol=3/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (chloroform:methanol=30:1 (v/v)) to obtain the title compound (1.5 g, 86%).

후처리

  1. temperaturerefluxed for 1 hour
  2. customThe mixed reaction solution
  3. customobtained in <Step 1> above, and
  4. temperaturefurther refluxed for 1 hour
  5. filtrationThe reaction mixture was filtered through a Celite pad under reduced pressure
  6. washwashed with ethanol and chloroform/2-propanol=3/1 (v/v)
  7. distillationThe resulting filtrate was distilled under reduced pressure
  8. dissolutiondissolved in ethanol
  9. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and brine
  10. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe concentrated compound was purified

출처 및 근거

ORD 기록
ord-8a8299b459db4dec9799b04f8afd3e9f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156852B2

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