Potassium hydroxy sulfite → HCID 67329343, compound

HRID 1754148Notes

Reaction equation

HRID 1754148 reaction equation
[OH:1]OS([O-])=O.[K+].[O:7]=[C:8]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH:9]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)[CH2:10][CH2:11][CH2:12][CH3:13]>CN(C=O)C>[O:7]=[C:8]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH:9]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([OH:1])=[O:19])=[CH:20][CH:21]=1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86674061HCID 86674061, compound

Product 1

HCID 67329343HCID 67329343, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxone (257 mg, 0.42 mmol) was added to a stirred solution of 4-(1-oxo-1-(piperidin-1-yl)hexan-2-yl)benzaldehyde (100 mg, 0.35 mmol) in DMF (5 mL) and the resulting mixture was stirred at room temperature for 16 hours. The DMF was removed in vacuo and the resulting residue was purified by flash column chromatography (50% EtOAc/hexane, Rf=0.4) to afford the desired compound as a pale yellow solid (68 mg. 64%). MP=142° C. 1H NMR (400 MHz, CDCl3) 0.86 (t, J=7 Hz, 3H); 1.05 (m, 1H); 1.15 (m, 1H); 1.2-1.6 (multiple signals, 8H); 1.71 (m, 1H); 2.10 (m, 1H); 3.33-3.43 (m, 3H); 3.69 (m, 1H); 3.77 (t, J=7 Hz, 1H); 7.38 (d, J=8.4 Hz, 2H); 8.02 (d, J=8.4 Hz, 2H). 13C NMR (75 MHz, CDCl3) 13.98, 22.68, 24.50, 25.55, 26.16, 30.04, 34.60, 43.32, 46.68, 48.82, 128.04, 130.50, 153.75, 170.59. HRMS (ESI+1 ion) m/z calcd for C18H26NO3 304.1907. found 304.1917.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe resulting residue was purified by flash column chromatography (50% EtOAc/hexane, Rf=0.4)

Sources & evidence

ORD record
ord-d44095d05b8b46efac92a5a640685c5f
Source dataset
uspto-grants-2015_10
Patent number
US09169223B2

Reaction notes

Loading…