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

HRID 969378Notes

Reaction equation

HRID 969378 reaction equation
[Cl:1][C:2]1[C:3]([CH2:18][CH3:19])=[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-].[CH2:28]([CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[CH2:29][CH2:30][CH3:31]>C(Cl)Cl.CO>[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]([CH2:18][CH3:19])=[C:4]([Cl:17])[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 689100026,8-Dichloro-4-(3-chloropropyl)-7-ethyl-4H-benzo[1,4]oxazin-3-one2×

Product 1

HCID 102879584-[3-(4-Butylpiperidin-1-yl)propyl]-6,8-dichloro-7-ethyl-4H-benzo[1,4]oxazin-3-oneYield 59%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

6,8-Dichloro-4-(3-chloro-propyl)-7-ethyl-4H-benzo[1,4]oxazin-3-one ((95MF52(2226)) (0.30 g, 0.93 mmol), K2CO3 (0.26 g, 1.86 mmol), NaI (0.28 g, 1.86 mmol) and 4-butylpiperidine (0.14 g, 0.98 mmol) were mixed according to GP13. CC (SiO2; CH2Cl2/MeOH 10:0.2-4) gave the title compound (95MF60) (0.24 g, 59%). 1H NMR (CDCl3) δ 7.10 (s, 1H), 4.65 (s, 2H), 3.93 (t, J=6.8 Hz, 2H), 2.95-2.81 (m, 4H), 2.33 (t, J=6.8 Hz, 2H), 1.90-1.78 (m, 4H), 1.66 (d, J=10.0 Hz, 2H) 1.30-1.13 (m, 12H), 0.88 (s, 3H); 13C NMR (CDCl3) δ 163.5, 140.6, 135.3, 128.2, 127.7, 123.2, 114.3, 67.9, 55.8, 54.4, 40.1, 36.4, 36.0, 32.7, 29.2, 24.8, 24.6, 23.1, 14.2, 12.7; HPLC-MS (ammonium acetate) [M+H]+=427.2.

Sources & evidence

ORD record
ord-fd508883a23d4d7b907c8094078bdd83
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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