Dimethylamine, hydrate → 4,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrile

HRID 2364857노트

반응식

HRID 2364857 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=3)[N:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[C:30]([Cu])#[N:31].[CH3:33][NH:34]C.O>CN(C)C=O>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([N:9]2[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([C:33]#[N:34])=[CH:3][CH:4]=3)[CH2:12][CH2:11][CH:10]2[C:13]2[CH:18]=[CH:17][C:16]([C:30]#[N:31])=[CH:15][CH:14]=2)=[CH:21][CH:22]=1)([CH3:28])([CH3:29])[CH3:27]

참가 물질

5

반응물 3

HCID 27521Dimethylamine, hydrateHCID 582268372,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)pyrrolidineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 672364944,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrile수율 50%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of Example 42C (1.0 g, 1.948 mmol) and CuCN (523 mg, 5.84 mmol) in Dimethylformamide (9.5 mL) was heated to 160° C. for 4.5 hours in a microwave. Mixture was poured into a dimethylamine/H2O mixture (1/10) and extracted with EtOAc (3×150 mL). The combined organics were washed with H2O and Brine. The organic was then dried (MgSO4), filtered and concentrated. Purification by chromatography (silica gel, 20% EtOAc in Hexanes) afforded 395 mg (50%) of the title compound. MS (ESI) m/z 406 (M+H)+.

후처리

  1. extractionextracted with EtOAc (3×150 mL)
  2. washThe combined organics were washed with H2O and Brine
  3. dry with materialThe organic was then dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica gel, 20% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-17fc48771cc94400bd228f6ab7cbcfb4
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691938B2

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