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

HRID 33467

反応式

HRID 33467 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f1581ed5899248c99cc9d8b5f38f94e0
出典データセット
uspto-grants-2008_09
特許番号
US07429603B2

関連ノート

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