1-Chloro-4-(chloromethyl)benzene → 3-Carbamoyl-1-(4-chlorobenzyl)piperidine

HRID 1280989

반응식

HRID 1280989 반응식
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([NH2:6])=[O:5])[CH2:2]1.CCN(CC)CC.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>CC#N.C(O)C.O>[C:4]([CH:3]1[CH2:7][CH2:8][CH2:9][N:1]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=2)[CH2:2]1)(=[O:5])[NH2:6]

참가 물질

8

반응물 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471TriethylamineHCID 929803-PiperidinecarboxamideHCID 516892Sodium Bicarbonate

생성물 1

HCID 28457973-Carbamoyl-1-(4-chlorobenzyl)piperidine수율 55.2%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

A solution of nipecotamide (6.40 g, 50 mmol) in CH3CN (150 mL) and ethanol (20 mL) was treated with Et3N (7.0 mL, 50 mmol) and 4-chlorobenzyl chloride (8.05 g, 50 mmol). The reaction mixture was stirred at 50° C. for 16 h. After cooling to room temperature, saturated aqueous NaHCO3 (50 mL) and water (150 mL) was added to the reaction mixture. The mixture was extracted with ethyl acetate (150 mL×3) and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give a pale red solid. The crude solid was washed with ether (100 mL) to afford 3-carbamoyl-1-(4-chlorobenzyl)piperidine (6.98 g, 54%).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (150 mL×3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a pale red solid
  7. washThe crude solid was washed with ether (100 mL)

출처 및 근거

ORD 기록
ord-8f36a84adc9b485faf9c12452aabe87d
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451842B1

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