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

HRID 85127

反応式

HRID 85127 の反応式
[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

参加物

5

反応物 2

HCID 7828801-[(3-Nitrophenyl)methyl]pyrrolidineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 10964073-(Pyrrolidin-1-ylmethyl)aniline収率 70%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-2045325230064db2aab90c3bced4e951
出典データセット
uspto-grants-2014_09
特許番号
US08846947B2

関連ノート

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