Sodium Iodide → 4-[3-(4-Butylpiperidin-1-yl)propyl]-8-isopropyl-4H-benzo[1,4]oxazin-3-one

HRID 2103237Notes

Reaction equation

HRID 2103237 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([CH:15]([CH3:17])[CH3:16])[C:9]=2[O:8][CH2:7][C:6]1=[O:18].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:27]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH2:28][CH2:29][CH3:30]>C(Cl)Cl.CO>[CH2:27]([CH:31]1[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][N:5]2[C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([CH:15]([CH3:17])[CH3:16])[C:9]=3[O:8][CH2:7][C:6]2=[O:18])[CH2:33][CH2:32]1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 689126914-(3-Chloropropyl)-8-isopropyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 102157574-[3-(4-Butylpiperidin-1-yl)propyl]-8-isopropyl-4H-benzo[1,4]oxazin-3-oneYield 39%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-(3-Chloropropyl)-8-isopropyl-4H-benzo[1,4]oxazin-3-one (95MF98) (0.112 g, 0.42 mmol), K2CO3 (0.115 g, 0.84 mmol), NaI (0.125 g, 0.84 mmol) and 4-butylpiperidine (0.062 g, 0.44 mmol) were mixed according to GP13. Prep TLC (SiO2; CH2Cl2/MeOH 10:1) gave the title compound (111MF02) (0.06 g, 39%). 1H NMR (CDCl3) δ 6.99-6.91 (m, 3H), 4.55 (s, 2H), 3.96 (t, J=7.4 Hz, 2H), 3.27 (m, 1H), 2.89 (d, J=11.2 Hz, 2H), 2.40 (t, J=7.2 Hz, 2H), 1.93-1.83 (m, 4H), 1.66 (d, J=9.6 Hz, 2H); 1.27-1.20 (m, 15H), 0.88 (t, J=6.8 Hz, 3H); 13C NMR (CDCl3) δ 164.7, 142.9, 137.5, 128.7, 122.6, 121.1, 112.9, 67.7, 56.0, 54.2, 39.9, 36.4, 35.9, 32.5, 29.1, 27.2, 24.9, 23.0, 22.7, 14.2.

Sources & evidence

ORD record
ord-9e8f711df56a4a3aaae39df0ef924903
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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