Sodium Iodide → HCID 10125819, compound

HRID 2102652Notes

Reaction equation

HRID 2102652 reaction equation
[Na+].[I-].C([O-])([O-])=O.[K+].[K+].[CH2:9]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH2:10][CH2:11][CH3:12].Cl[CH2:20][CH2:21][CH2:22][N:23]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH2:25][C:24]1=[O:33]>C(#N)C.CO>[CH2:9]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:20][CH2:21][CH2:22][N:23]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][CH2:25][C:24]2=[O:33])[CH2:15][CH2:14]1)[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 233451504-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 10125819HCID 10125819, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

NaI (1.33 g, 8.87 mmol), K2CO3 (1.23 g, 8.90 mmol), and 4-butylpiperidine (0.66 g, 4.71 mmol) in acetonitrile (10 mL) were stirred at rt. 4-(3-chloropropyl)-4H-benzo[1,4]oxazin-3-one (1.0 g, 4.43 mmol) in acetonitrile (15 mL) was added via a syringe. The reaction was stirred at 60° C. for 13 hours and then at 80° C. for another 5 hours under nitrogen atmosphere and concentrated in vacuo. Water (150 mL) was added and the reaction mixture was extracted with ethyl acetate (3×150 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuo to give 1.58 g of crude. The crude product was subjected to CC[eluent:EtOAC:MeOH(100:1-5%)] to give the pure title compound. Yield 0.82 g 56.0% HPLC-MS [M+H]+ 331 (UV/MS(%)=100/99. 1H NMR (CDCl3): δ 0.88 (t, 3H), 1.21 (m, 6H), 1.26 (m, 3H), 1.66 (d, 2H), 1.86 (m, 4H), 2.37 (t, 2H), 2.86, (d, 2H), 3.97 (t, 2H), 4.58 (s, 2H), 6.99 (m, 3H), 7.11 (d, 1H), 13C NMR (CDCl3): δ 14.22, 23.04, 24.90, 29.17, 32.68, 35.95, 36.46, 39.74, 54.31, 56.02, 67.77, 115.26, 117.15, 122.83, 123.83, 128.78, 145.50, 164.34.

Workup

  1. waitat 80° C. for another 5 hours under nitrogen atmosphere
  2. concentrationconcentrated in vacuo
  3. additionWater (150 mL) was added
  4. extractionthe reaction mixture was extracted with ethyl acetate (3×150 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give 1.58 g of crude

Sources & evidence

ORD record
ord-09b9f2fa505b4c7a9e463e6cc0f88514
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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