5-Nitrofurfural → 5-(Nitro-furan-2-ylmethyl)-(2-piperidin-1-yl-phenyl)-amine

HRID 33467

반응식

HRID 33467 반응식
[N:1]1([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:14]([C:17]1OC(C=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(O[BH-](O[C:34](=[O:36])[CH3:35])OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N+:14]([CH:17]([C:18]1[O:36][CH:34]=[CH:35][CH:19]=1)[C:11]1[CH:12]=[CH:13][C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]([NH2:9])[CH:10]=1)([O-:16])=[O:15]

참가 물질

5

반응물 3

HCID 127745-NitrofurfuralHCID 4587952-(Piperidin-1-yl)anilineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 865957225-(Nitro-furan-2-ylmethyl)-(2-piperidin-1-yl-phenyl)-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2-piperidinoaniline (1 mmol), 5-nitro-furan-2-carbaldehyde (1.1 mmol) and sodium triacetoxyborohydride (“NaBH(OAc)3”) (2 mmol) in anhydrous DCM (10 mL) was stirred 16 h at room temperature. The mixture was then washed successively with water, dilute aqueous sodium hydroxide (“NaOH”), water and brine before being dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residual oil by flash silica gel chromatography yielded the product. MS: 301 (M+1). LC/MS purity: 100%. 1H NMR (CDCl3, 300 MHz): δ 7.25 (d, 1H), 7.15-6.95 (m, 2H), 6.75 (t, 1H), 6.55 (d, 1H), 5.4 (bs, 1H), 4.45 (s, 2H), 2.8 (bm, 4H), 1.8-1.5 (bm, 6H).

후처리

  1. washThe mixture was then washed successively with water, dilute aqueous sodium hydroxide (“NaOH”), water and brine
  2. dry with materialbefore being dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residual oil by flash silica gel chromatography
  6. customyielded the product

출처 및 근거

ORD 기록
ord-f1581ed5899248c99cc9d8b5f38f94e0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429603B2

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