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Sodium Iodide → 4-[3-(4-Cyclopropylmethoxypiperidin-1-yl)propyl]-6-fluoro-4H-benzo[1,4]oxazin-3-one

HRID 1191521
Notes
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Reaction equation

HRID 1191521 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16].[CH:17]1([CH2:20][O:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:19][CH2:18]1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:17]1([CH2:20][O:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][N:5]3[C:10]4[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=4[O:8][CH2:7][C:6]3=[O:16])[CH2:24][CH2:23]2)[CH2:18][CH2:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 171780104-(Cyclopropylmethoxy)piperidineHCID 68910689HCID 68910689, compound

Product 1

HCID 116319134-[3-(4-Cyclopropylmethoxypiperidin-1-yl)propyl]-6-fluoro-4H-benzo[1,4]oxazin-3-oneYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A 4 mL vial was charged with 4-(3-chloropropyl)-6-fluoro-4H-benzo[1,4]oxazin-3-one (0.097 g, 0.4 mmol), 4-cyclopropylmethoxypiperidine (0.042 g, 0.27 mmol), NaI (0.075 g, 0.5 mmol), and K2CO3 (0.069 g, 0.5 mmol) in MeCN (1 mL) and shaken at 500 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 followed by flash column chromatography (SiO2; EtOAc) to give the title compound (0.056 g, 57%). 1H NMR (CDCl3) δ 6.80-6.71 (m, 2H), 6.52-6.47 (m, 1H), 4.38 (s, 2H), 3.77 (t, J=7.2 Hz, 2H), 3.17-3.13 (m, 1H), 3.11 (d, J=6.8 Hz, 2H), 2.59-2.56 (m, 2H), 2.19 (t, J=6.8 Hz, 2H), 1.95-1.89 (m, 2H), 1.75-1.62 (m, 4H), 1.50-1.41 (m, 2H), 0.89-0.86 (m, 1H), 0.38-0.33 (m, 2H), 0.04-0.00 (m, 2H); 13C NMR (CDCl3) δ 164.1, 158.3, 141.2, 129.8, 117.4, 109.4, 102.9, 74.7, 72.5, 67.6, 55.1, 51.4, 39.8, 31.3, 24.6, 10.9, 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-981c7276fc694070898fd846c61feebc
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680115B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes