Pyrrolidine → 2-(Pyrrolidin-1-yl)-4-amino-m-xylene

HRID 1182266노트

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HRID 1182266 반응식
Br[C:2]1[C:3]([CH3:10])=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[N:11]1([C:2]2[C:3]([CH3:10])=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=2[CH3:8])[CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 123959063-Bromo-2,4-dimethylanilineHCID 23676156Sodium t-butoxide

생성물 1

HCID 204949532-(Pyrrolidin-1-yl)-4-amino-m-xylene

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

To a solution of the 3-bromo-2,4-dimethylphenylamine (0.6 g, 3.0 mmol) in toluene (10 mL) and pyrrolidine (1.25 mL, 15 mmol) was added sodium-t-butoxide (0.86 g, 9 mmol, 3eq). The suspension was deoxygenated by passing a stream of N2 gas through the mixture for approximately 5–10 minutes before introducing the tris(dibenzilidene)dipalladium(0) (Pd2(dba)3) (27 mg) and rac-2,2′Bis(diphenylphosphino)-1,1′binaphthyl (BINAP) (25 mg). The nitrogen stream continued 10 minutes before heating at 100° C. overnight. The reaction mixture was cooled, acidified with HCl (2N) and extracted with diethyl ether. The aqueous layer was adjusted basic and re-extracted with ethyl acetate. The organic layer was dried over sodium sulfate, decanted and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, gradient elution with 6:1 to 4:1 hexanes to ethyl acetate) to give the desired 2-(pyrrolidin-1-yl)-4-amino-m-xylene.

후처리

  1. customThe suspension was deoxygenated
  2. customfor approximately 5–10 minutes
  3. additionbefore introducing the tris(dibenzilidene)dipalladium(0) (Pd2(dba)3) (27 mg) and rac-2,2′Bis(diphenylphosphino)-1,1′binaphthyl (BINAP) (25 mg)
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with diethyl ether
  6. extractionre-extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customdecanted
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (silica gel, gradient elution with 6:1 to 4:1 hexanes to ethyl acetate)

출처 및 근거

ORD 기록
ord-760f60a7e9f14de4be0929e705825a2b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288538B2

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