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

HRID 1750883ノート

反応式

HRID 1750883 の反応式
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

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 57678518HCID 57678518、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8a8299b459db4dec9799b04f8afd3e9f
出典データセット
uspto-grants-2015_10
特許番号
US09156852B2

反応ノート

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