Furfurylamine → 1-(Furan-2-yl)-N-[(thiophen-2-yl)methyl]methanamine

HRID 1850237Notes

Reaction equation

HRID 1850237 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:1][NH:7][CH2:13][C:9]1[S:8][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 3438FurfurylamineHCID 73642-ThiophenecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10884801-(Furan-2-yl)-N-[(thiophen-2-yl)methyl]methanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of furfurylamine (2.0 g, 0.0206 mol) and 2-thiophenecarboxaldehyde (2.31 g, 0.0206 mol) in dichloromethane (60 ml) was stirred at room temperature for 5 minutes before adding portionwise sodium triacetoxyborohydride (5.24 g, 0.0247 mol). After addition was complete (approx. 2 minutes), the reaction mixture was stirred at room temperature for 3 hours and washed with sat'd NaHCO3 (aq.), dried (MgSO4), filtered and concentrated. The product mixture was purified by flash chromatography (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc to 1:1 hexanes:EtOAc) to obtain the amine as a light yellow oil, 1.65 g (41%). MS (APCI): (M+1)+=194; 1H-NMR is consistent with structure.

Workup

  1. additionAfter addition
  2. custom(approx. 2 minutes)
  3. stirringthe reaction mixture was stirred at room temperature for 3 hours
  4. washwashed with sat'd NaHCO3 (aq.)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product mixture was purified by flash chromatography (silica gel 60, 230-400 mesh, 4:1 hexanes:EtOAc to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-28b0432ece8540ad90398a16a9021952
Source dataset
uspto-grants-2015_02
Patent number
US08957075B2

Reaction notes

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