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

HRID 1711212Notes

Reaction equation

HRID 1711212 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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), 6.4 (d, 1H), 5.4 (bs, 1H), 4.45 (s, 2H), 2.8 (bm, 4H), 1.8-1.5 (bm, 6H).

Workup

  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

Sources & evidence

ORD record
ord-013e2fe47eb843389014edee83f4de5b
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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