Ammonium Chloride → 4-(Piperidin-1-yl)aniline

HRID 1665637

反応式

HRID 1665637 の反応式
[Cl-].[NH4+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([O-])=O>O.C1COCC1.[Fe]>[N:12]1([C:9]2[CH:8]=[CH:7][C:6]([NH2:3])=[CH:11][CH:10]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 81049Piperidine, 1-(4-nitrophenyl)-

生成物 1

HCID 4135014-(Piperidin-1-yl)aniline収率 102.1%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

Ammonium chloride (228 mg, 4.2 mmol) in water (4 mL) was added to a solution of 1-(4-nitro-phenyl)-piperidine (220 mg, 1.0 mmol) in THF (6 mL) and the resulting mixture was stirred at 75° C. for 30 minutes. Iron powder (238 mg, 4.2 mmol) was then added portion wise and the mixture stirred for 5 hours at 75° C. The reaction mixture was filtered over celite, the filtrate was basified with sodium bicarbonate solution and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 180 mg (96%) of 4-Piperidin-1-yl-phenylamine. LCMS: 177.13 (M+1)+, 80.6%, 1H NMR: (DMSO-d6): δ 6.67 (m, 2H), 6.47 (m, 2H), 4.51 (s, 2H), 2.57 (t, 4H), 1.6 (q, 4H), 1.49 (m, 2H)

後処理

  1. stirringthe mixture stirred for 5 hours at 75° C
  2. filtrationThe reaction mixture was filtered over celite
  3. extractionthe product extracted with ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d627c5649ddf43488284ccc7edd431d2
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

関連ノート

読み込み中…