Tetrahydrofuran → HCID 66710101, compound

HRID 1256003Notes

Reaction equation

HRID 1256003 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C1COCC1>ClCCCl>[CH:19]1([NH:22][CH:15]2[CH2:16][CH2:17][N:12]([C:5]3[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:13][CH2:14]2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 259188571-(3-Methoxy-4-nitrophenyl)piperidin-4-one2×

Product 1

HCID 66710101HCID 66710101, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-(3-Methoxy-4-nitrophenyl)piperidin-4-one (INTERMEDIATE 18, 0.70 g, 2.80 mmol), cyclopropanamine (0.160 g, 2.80 mmol) and sodium triacetoxyborohydride (0.889 g, 4.20 mmol) in DCE (15 mL)/THF (5 mL) were stirred at 25° C. for 2 h. The reaction mixture was concentrated in vacuo. The crude residue was taken up in EtOAc and washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (10% MeOH/EtOAc) to give the title product (0.76 g, 93%). m/z 292.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by chromatography on silica gel (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-604ea29e381347c5a2f27d071102251a
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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