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

HRID 2102574Notes

Reaction equation

HRID 2102574 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:16]([O-:19])([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]>CC#N>[CH2:24]([CH:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][N:5]2[C:10]3[CH:11]=[C:12]([O:19][CH3:16])[CH:13]=[CH:14][C:9]=3[O:8][CH2:7][C:6]2=[O:15])[CH2:30][CH2:29]1)[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

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

Product 1

HCID 102869544-[3-(4-Butylpiperidin-1-yl)propyl]-6-methoxy-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A 7 mL vial was charged with 4-(3-chloropropyl)-4H-benzo[1,4]oxazin-3-one (1.0 equiv), K2CO3 (2.0 equiv), NaI (2.0 equiv) and 4-Butylpiperidine (1.05 equiv) in 5 mL dry MeCN and shaken at 60° C. for 48 h. The reaction mixture was evaporated to dryness, diluted with 10 mL H2O, extracted into CH2Cl2 (3×13 mL), and filtered through a PTFF Whatman filter. The combined organic layers were evaporated to dryness and purified by CC (Heptane/EtOAc or CH2Cl2/MeOH) or prep TLC (Heptane/EtOAc or CH2Cl2/MeOH).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiondiluted with 10 mL H2O
  3. extractionextracted into CH2Cl2 (3×13 mL)
  4. filtrationfiltered through a PTFF Whatman
  5. filtrationfilter
  6. customThe combined organic layers were evaporated to dryness
  7. custompurified by CC (Heptane/EtOAc or CH2Cl2/MeOH) or prep TLC (Heptane/EtOAc or CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-85d04ecde9ea4e2d94e56d6ffd68a5a2
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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