Tetrapropylammonium → HCID 57625190, compound

HRID 658977Notes

Reaction equation

HRID 658977 reaction equation
[CH2:1]([C:8]1[CH:25]=[CH:24][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][C:16]=2[F:23])=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>CC#N>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][C:16]=2[F:23])=[O:13])=[CH:24][CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 57625193HCID 57625193, compound

Product 1

HCID 57625190HCID 57625190, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-benzyl-N-(2-fluoro-4-(hydroxymethyl)phenyl)benzamide (200 mg, 0.60 mmol), 4-methylmorpholine N-oxide (140 mg, 1.2 mmol), and 4 A molecular sieves (1 g) in 10 ml of CH3CN was treated with tetrapropylammonium perruthnate (10 mg, 0.03 mmol) and the resulting mixture was stirred at room temperature for 12 hours. The solids were filtered and the filtrated was concentrated. The residue was purified on ISCO system (80% hexane in dichloromethane) to give a pure product as a white crystalline: 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 8.80 (t, J=8.0 Hz, 1H), 8.25 (s, 1H), 7.84 (d, J=7.2 Hz, 2H), 7.74 (d, J=8.4 Hz, 1H), 7.69 (d, J=10.8 Hz, 1H), 7.19-7.37 (m, 6H), 4.07 (s, 2H).

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe filtrated was concentrated
  3. customThe residue was purified on ISCO system (80% hexane in dichloromethane)
  4. customto give a pure product as a white crystalline: 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 8.80 (t, J=8.0 Hz, 1H), 8.25 (s, 1H), 7.84 (d, J=7.2 Hz, 2H), 7.74 (d, J=8.4 Hz, 1H), 7.69 (d, J=10.8 Hz, 1H), 7.19-7.37 (m, 6H), 4.07 (s, 2H)

Sources & evidence

ORD record
ord-a2e287c337ab4aaf9b7e0e144fcb2d73
Source dataset
uspto-grants-2011_12
Patent number
US08080542B2

Reaction notes

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