Methylamine → HCID 57185316, compound

HRID 991452Notes

Reaction equation

HRID 991452 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.[CH3:12][NH2:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C1COCC1.C(O)(=O)C>[O:1]1[CH:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:4]2[CH:3]=[C:2]1[CH2:10][NH:13][CH3:12]

Participants

7

Reactant 3

HCID 6329MethylamineHCID 613412-BenzofurancarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57185316HCID 57185316, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of benzofuran-2-carboxaldehyde (1.50 g) and 4 Å molecular sieves in dichloroethane (50 ml) under an atmosphere of nitrogen was added methylamine in THF (2.0M, 10.3 ml) and acetic acid (1.23 g). Stirring was continued for 2 h before sodium triacetoxyborohydride (2.18 g) was added and stirring as continued overnight. The mixture was filtered, absorbed onto silica gel and chromatographed eluting with dichloromethane/methanol (9:1) to yield the title compound (1.05 g, 64%) as an off-white solid.

Workup

  1. additionwas added
  2. stirringstirring as continued overnight
  3. filtrationThe mixture was filtered
  4. customabsorbed onto silica gel
  5. customchromatographed
  6. washeluting with dichloromethane/methanol (9:1)

Sources & evidence

ORD record
ord-24ea8903028e44d9abdd862329a74784
Source dataset
uspto-grants-2002_10
Patent number
US06465468B1

Reaction notes

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