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

HRID 1665637

반응식

HRID 1665637 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 4135014-(Piperidin-1-yl)aniline수율 102.1%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-d627c5649ddf43488284ccc7edd431d2
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

연결된 노트

불러오는 중…