Sodium Iodide → HCID 68912810, compound

HRID 2102566Notes

Reaction equation

HRID 2102566 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH2:9][S:8][C:7]2[CH:12]=[CH:13][N:14]=[CH:15][C:6]1=2.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:24]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[CH2:25][CH2:26][CH3:27]>CCCCCCC.CCOC(C)=O>[CH2:24]([CH:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][N:5]2[C:10](=[O:11])[CH2:9][S:8][C:7]3[CH:12]=[CH:13][N:14]=[CH:15][C:6]2=3)[CH2:30][CH2:29]1)[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 68910325HCID 68910325, compound

Product 1

HCID 68912810HCID 68912810, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

4-(3-Chloropropyl)-4H-pyrido[4,3-b][1,4]thiazin-3-one (81MF939b) (0.14 g, 0.57 mmol), K2CO3 (0.16 g, 11.4 mmol), NaI (0.18 g, 11.4 mmol) and 4-butylpiperidine (0.09 g, 0.60 mmol) were mixed according to GP12. CC (SiO2; Heptane/EtOAc 10:1-4) gave the title compound (81MF939) (0.064 g, 32%). 1H NMR (CDCl3) δ 8.48 (s, 1H), 8.17 (d, J=5.2 Hz, 1H), 7.25 (d, J=4.8 Hz, 1H), 4.06-4.12 (m, 2H), 3.41 (s, 2H), 2.82 (d, J=11.2, 2H), 2.33 (t, J=6.8 Hz, 2H), 1.83-1.89 (m, 4H), 1.64 (d, J=9.2 Hz, 2H), 1.16-1.29 (m, 9H), 0.87 (t, J=6.8 Hz, 3H); 13C NMR (CDCl3) δ 163.91, 143.84, 138.92, 136.20, 134.04, 122.31, 55.80, 54.32, 43.29, 36.43, 35.99, 32.68, 30.78, 29.19, 25.20, 23.05, 14.24.

Sources & evidence

ORD record
ord-3962dd0733144452b6f4c6a3ce1e52ac
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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