Potassium Carbonate → 1-[(3-Nitrophenyl)methyl]pyrrolidine

HRID 85126

반응식

HRID 85126 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

생성물 1

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cab39a03811c4574a2ea895293bed978
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846947B2

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