Sodium Iodide → 4-[3-(3-Butylidene-8-aza-bicyclo[3.2.1]oct-8-yl)-propyl]-4H-benzo[1,4]oxazin-3-one

HRID 2102572Notes

Reaction equation

HRID 2102572 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH:24](=[C:28]1[CH2:34][CH:33]2[NH:35][CH:30]([CH2:31][CH2:32]2)[CH2:29]1)[CH2:25][CH2:26][CH3:27]>C(Cl)Cl.CO>[CH:24](=[C:28]1[CH2:29][CH:30]2[N:35]([CH2:2][CH2:3][CH2:4][N:5]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[O:8][CH2:7][C:6]3=[O:15])[CH:33]([CH2:32][CH2:31]2)[CH2:34]1)[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 233451504-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-oneHCID 689110833-Butylidene-8-azabicyclo[3.2.1]octane

Product 1

HCID 689082164-[3-(3-Butylidene-8-aza-bicyclo[3.2.1]oct-8-yl)-propyl]-4H-benzo[1,4]oxazin-3-oneYield 41.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-(3-Chloropropyl)-4H-benzo[1,4]oxazin-3-one (81MF08) (0.030 g, 0.13 mmol), K2CO3 (0.037 g, 0.26 mmol), NaI (0.040 g, 0.27 mmol) and 3-butylidene-8-azabicyclo[3.2.1]octane (0.029 g, 0.17 mmol) were mixed according to GP12. Prep TLC (SiO2; CH2Cl2/MeOH 10:1) gave the title compound (81MF24) (0.019 g, 41%). 1H NMR (CDCl3) δ 7.22-7.19 (m, 1H), 7.05-6.96 (m, 3H), 5.24 (t, J=7.2 Hz, 1H), 5.08 (s, 2H), 4.06 (t, J=6.4 Hz, 2H), 2.61 (t, J=6.8 Hz, 2H), 2.30 (s, 2H), 2.03-1.83 (m, 7H), 1.58-1.43 (m, 2H), 1.39-1.22 (m, 3H), 0.89 (m, 3H); 13C NMR (CDCl3) δ 164.5, 145.5, 131.4, 128.7, 127.9, 124.0, 123.0, 117.1, 115.5, 67.8, 60.4, 60.2, 48.8, 41.0, 39.6, 33.7, 29.5, 26.8, 26.4, 25.8, 23.2, 13.9.

Sources & evidence

ORD record
ord-31fb6760d6574c6f848c4c47d7d956ab
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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