1-[(3-Nitrophenyl)methyl]pyrrolidine → 3-(Pyrrolidin-1-ylmethyl)aniline

HRID 85127

반응식

HRID 85127 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)([O-])=O.[H][H]>CCO.[Pd]>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([CH:15]=[CH:14][CH:13]=2)[NH2:1])[CH2:12][CH2:11][CH2:10][CH2:9]1

참가 물질

5

반응물 2

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 10964073-(Pyrrolidin-1-ylmethyl)aniline수율 70%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

1-(Bromomethyl)-3-nitrobenzene (51; 5 g, 23.1 mmol) was taken up in 100 mL of anhydrous THF along with pyrrolidine (2.3 mL, 27.72 mmol) and K2CO3 (4.8 g, 34.6 mmol). The reaction mixture was stirred at room temperature for 18 h and then filtered. The filtrate was concentrated under reduced pressure to afford 1-(3-nitrobenzyl)pyrrolidine 52. This material 52 was taken up in 100 mL of absolute EtOH and 10% Pd on C (300 mg) was added. The resulting reaction mixture was stirred at room temperature under 1 atm of hydrogen for 18 h. The mixture was then filtered through a pad of Celite and the filtrate was concentrated under reduced pressure to afford 2.81 g of 3-(pyrrolidin-1-ylmethyl)aniline 53 (70%).

후처리

  1. customThe resulting reaction mixture
  2. filtrationThe mixture was then filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2045325230064db2aab90c3bced4e951
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846947B2

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