Hexane → N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide

HRID 247747

반응식

HRID 247747 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].[CH2:15]([Li])[CH2:16][CH2:17][CH3:18].[CH3:20][CH2:21][CH2:22]CCC.C(=[CH:33][NH2:34])C1C=CC=CC=1>C1COCC1.CCOCC>[CH3:33][NH:34][CH:15]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:18][CH:17]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 155076Ethenamine, 2-phenyl-HCID 27340052,2,2'-TrimethylpropionanilideHCID 178418339Butyllithium2회

생성물 1

HCID 10968937N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide수율 78%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A stirred solution of N-[(2-methyl)phenyl]-2,2-dimethylpropanamide (95.6 g, 0.5 mol) in THF (500 ml, dried over 4 Å molecular sieves) was cooled to 0° C. and treated with 1.6M n-butyllithium in hexane (630 ml, 1.0 mol). The addition of n-butyllithium was complete after 45 minutes. During the addition, the temperature of the mixture was maintained below 10° C. with external cooling. The resultant dianion solution was aged (about 1-2 hrs) at 0° C. until the homogeneous orange solution became a white heterogeneous slurry. The dianion was then quenched with N-benzylidenemethylamine (63.7 g, 0.6 mol) and aged for 30 minutes at 15°-25° C. The reaction mixture was diluted with ether (200 ml), treated with crushed ice (200 g), and stirred for 15 minutes. The organic phase was separated, washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residual oil was crystallized from hexane (400 ml) at 5° C. to give N-[2-(2-methylamino-2-phenylethyl)phenyl]-2,2-dimethylpropanamide (121.2 g, 0.39 mol) in 78% yield. The product had a melting point of 85°-86° C.

후처리

  1. additionDuring the addition
  2. temperaturethe temperature of the mixture was maintained below 10° C. with external cooling
  3. custom(about 1-2 hrs)
  4. customat 0° C.
  5. waitaged for 30 minutes at 15°-25° C
  6. customThe organic phase was separated
  7. washwashed with saturated sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residual oil was crystallized from hexane (400 ml) at 5° C.

출처 및 근거

ORD 기록
ord-2719aa70f12b4ba4b2d8f113f5f3a760
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04709093

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