Benzophenone imine → 3-(Benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one

HRID 626874노트

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HRID 626874 반응식
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[C:17]1=[O:22]>ClCCCl>[C:1](=[N:14][CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[C:17]1=[O:22])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 136809Benzophenone imineHCID 457911333-Amino-1-methylpyrrolidin-2-one

생성물 1

HCID 896489983-(Benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one수율 88.7%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
95 °C

실험 절차

Benzophenone imine (200.04 g, 1103.8 mmol) was added dropwise over 20 minutes to a stirred solution of 3-amino-1-methylpyrrolidine-2-one (120 g, 1051.2 mmol) in DCE (1000 mL) at ambient temp under nitrogen in a 2 L flask fitted with a magnetic stirrer bar. The reagent was washed with further DCE (100 mL). The stirred solution was heated at reflux on a heat-on block at a block temp of 95° C. for 7 h, using a N2 bubbler with exhaled gas passing through a safety trap then into 2 L of water via an upturned funnel (for scrubbing NH3 gas, estimated to be approx 23 L). The reaction was left to stand at ambient temp overnight under N2. The mixture was evaporated to a thick, off-white oil. To this was added Et2O (700 ml) and to this stirred solution, as it began to crystallize, was added iso-hexane (700 ml) over 2 minutes. The mixture was stirred for 1 h then filtered under suction and washed with Et2O/iso-hexane (1:1) (500 ml). The white solid was dried at 35° C. under vacuum for 3 h to afford 3-(benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one (D1) (259.4 g, 88.6%). The NMR was consistent with pure material.

후처리

  1. customfitted with a magnetic stirrer bar
  2. washThe reagent was washed with further DCE (100 mL)
  3. temperatureThe stirred solution was heated
  4. waitThe reaction was left
  5. customThe mixture was evaporated to a thick, off-white oil
  6. additionTo this was added Et2O (700 ml)
  7. customto crystallize
  8. additionwas added iso-hexane (700 ml) over 2 minutes
  9. filtrationthen filtered under suction
  10. washwashed with Et2O/iso-hexane (1:1) (500 ml)
  11. customThe white solid was dried at 35° C. under vacuum for 3 h

출처 및 근거

ORD 기록
ord-74d9836d15ce49a399e22f2aa1c1fcdb
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309254B2

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