Sodium Iodide → 4-[3-(4-Butylpiperidin-1-yl)propyl]-6,8-dichloro-7-methyl-4H-benzo[1,4]oxazin-3-one

HRID 969360Notes

Reaction equation

HRID 969360 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([Cl:17])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14]Cl)[C:6]=2[CH:16]=1.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]>CCCCCCC.CCOC(C)=O>[CH2:27]([CH:31]1[CH2:36][CH2:35][N:34]([CH2:14][CH2:13][CH2:12][N:7]2[C:6]3[CH:16]=[C:2]([Cl:1])[C:3]([CH3:18])=[C:4]([Cl:17])[C:5]=3[O:10][CH2:9][C:8]2=[O:11])[CH2:33][CH2:32]1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 689125586,8-Dichloro-4-(3-chloropropyl)-7-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 101944934-[3-(4-Butylpiperidin-1-yl)propyl]-6,8-dichloro-7-methyl-4H-benzo[1,4]oxazin-3-oneYield 47.3%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

6,8-Dichloro-4-(3-chloropropyl)-7-methyl-4H-benzo[1,4]oxazin-3-one (81MF2225b), (2.44 g, 7.92 mmol), K2CO3 (2.19 g, 15.84 mmol), NaI (2.37 g, 15.84 mmol) and 4-butylpiperidine (1.172 g, 8.3 mmol) were mixed according to GP11. CC (SiO2; Heptane/EtOAc 10:1-4) gave the title compound (81MF2225F) (1.55 g, 47%). 1H NMR (CDCl3) δ 7.11 (s, 1H), 4.65 (s, 2H), 3.93 (t, 2H), 2.86, (d, 2H), 2.41 (s, 3H), 2.33 (t, 2H), 1.92-1.77 (m, 4H), 1.65 (d, 2H), 1.31-1.19 (m, 9H), 0.88 (t, 3H); 13C NMR (CDCl3) δ 163.5, 140.5, 129.9, 128.1, 123.7, 114.0, 67.9, 55.8, 54.4, 40.1, 36.4, 36.0, 32.6, 29.2, 24.8, 23.1, 17.2, 14.2.

Sources & evidence

ORD record
ord-a91f53b940584e5a9d4880d4c0c93fbb
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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