Sodium Iodide → HCID 10215661, compound

HRID 2103222Notes

Reaction equation

HRID 2103222 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([CH2:11][CH2:12][CH2:13]Cl)[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:25]([CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH2:26][CH2:27][CH3:28]>CCCCCCC.CCOC(C)=O>[CH2:25]([CH:29]1[CH2:34][CH2:33][N:32]([CH2:13][CH2:12][CH2:11][N:6]2[C:5]3[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][C:4]=3[O:9][CH2:8][C:7]2=[O:10])[CH2:31][CH2:30]1)[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 68910501HCID 68910501, compound

Product 1

HCID 10215661HCID 10215661, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

7-Chloro-4-(3-chloropropyl)-4H-benzo[1,4]oxazin-3-one (81MF2271 b) (1.953 g, 7.49 mmol), K2CO3 (2.07 g, 14.9 mmol), NaI (2.24 g, 14.9 mmol) and 4-butylpiperidine (1.11 g, 7.86 mmol) were mixed according to GP11. CC (SiO2; Heptane/EtOAc 10:1-4) gave the title compound (81MF2271x) (2.46 g, 90%). 1H NMR (CDCl3) δ 7.08-6-96 (m, 3H), 4.57 (s, 2H), 3.95 (t, J=7.2 Hz, 2H), 2.85 (d, J=10.8 Hz, 2H), 2.35 (t, J=7.2 Hz, 2H), 1.93-1.78 (m, 4H), 1.66 (d, J=9.2 Hz, 2H), 1.31-1.18 (m, 9H), 0.88 (t, J=6.4 Hz, 3H); 13C NMR (CDCl3) δ 163.7, 146.0, 128.7, 127.7, 122.7, 117.6, 116.1, 67.7, 55.9, 54.3, 39.9, 36.5, 36.0, 32.7, 29.2, 24.8, 23.1, 14.2.

Sources & evidence

ORD record
ord-e77d9f4dc33d4f2da53d378399173ee3
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

Loading…