Sodium Iodide → HCID 11523039, compound

HRID 1986851Notes

Reaction equation

HRID 1986851 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].[CH:16]1([CH2:19][O:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:18][CH2:17]1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:16]1([CH2:19][O:20][CH:21]2[CH2:26][CH2:25][N:24]([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])[CH2:23][CH2:22]2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 171780104-(Cyclopropylmethoxy)piperidineHCID 233451504-(3-chloropropyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 11523039HCID 11523039, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 4 mL vial was charged with 4-(3-chloropropyl)-4H-benzo[1,4]oxazin-3-one (0.068 g, 0.3 mmol), 4-cyclopropylmethoxypiperidine (0.047 g, 0.3 mmol), NaI (0.075 g, 0.5 mmol), and K2CO3 (0.069 g, 0.5 mmol) in MeCN (1 mL) and shaken at 50° for 20 h. The reaction mixture was quenched with water and the product extracted into EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The product was purified by cation exchange column chromatography to give the title compound (0.076 g, 74%). 1H NMR (CDCl3) d 6.96-6.93 (m, 1H), 6.87-6.80 (m, 3H), 4.41 (s, 2H), 3.81 (t, J=7.4 Hz, 2H), 3.16-3.10 (m, 1H), 3.11 (d, J=6.8 Hz, 2H), 2.62-2.57 (m, 2H), 2.22 (t, J=7.0 Hz, 2H), 1.94-1.89 (m, 2H), 1.75-1.64 (m, 4H), 1.48-1.39 (m, 2H), 0.89-0.86 (m, 1H), 0.38-0.33 (m, 2H), 0.04-0.00 (m, 2H); 13C NMR (CDCl3) d 164.2, 145.3, 128.6, 123.7, 122.7, 117.0, 115.0, 74.8, 72.6, 67.6, 55.3, 51.4, 39.5, 31.5, 24.8, 11.0, 3.0.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe product extracted into EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by cation exchange column chromatography

Sources & evidence

ORD record
ord-83d852053d0c4c4380bb7174fd7bcdf5
Source dataset
uspto-grants-2009_06
Patent number
US07550459B2

Reaction notes

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