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

HRID 969365Notes

Reaction equation

HRID 969365 reaction equation
[Cl:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[CH:4][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-].[CH2:28]([CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[CH2:29][CH2:30][CH3:31]>CCCCCCC.CCOC(C)=O>[CH2:28]([CH:32]1[CH2:37][CH2:36][N:35]([CH2:14][CH2:13][CH2:12][N:7]2[C:6]3[CH:16]=[C:2]([Cl:1])[C:3]([N+:17]([O-:19])=[O:18])=[CH:4][C:5]=3[O:10][CH2:9][C:8]2=[O:11])[CH2:34][CH2:33]1)[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 689109146-Chloro-4-(3-chloropropyl)-7-nitro-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 101268824-[3-(4-Butylpiperidin-1-yl)propyl]-6-chloro-7-nitro-4H-benzo[1,4]oxazin-3-oneYield 42%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

6-Chloro-4-(3-chloropropyl)-7-nitro-4H-benzo[1,4]oxazin-3-one (81MF2253b) (1.23 g, 4.05 mmol), K2CO3 (1.12 g, 8.09 mmol), NaI (1.21 g, 8.09 mmol) and 4-butylpiperidine (0.60 g, 4.24 mmol) were mixed according to GP11. CC (SiO2; Heptane/EtOAc 10:1-4) gave the title compound (81MF2253x) (0.698 g, 42%). 1H NMR (CDCl3) δ 7.61 (s, 1H), 7.36 (s, 1H), 4.66, (s, 2H), 3.99 (t, J=6.8 Hz, 2H), 2.85 (d, J=11.2 Hz, 2H), 2.34 (t, J=6.4 Hz, 2H), 1.94-1.80 (m, 4H), 1.67 (d, J=10.0 Hz, 2H), 1.31-1.20 (m, 9H), 0.88 (t, J=6.4 Hz, 3H); 13C NMR (CDCl3) δ 163.4, 143.4, 141.9, 133.9, 122.1, 117.7, 114.8, 67.5, 55.5, 54.4, 40.5, 36.4, 36.0, 32,6, 29.2, 24.6, 23.0, 14.2.

Sources & evidence

ORD record
ord-2843ebfcd41447e8a22ca0e546c0e7d5
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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