Ammonia → HCID 58932541, compound

HRID 853891Notes

Reaction equation

HRID 853891 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]2([O:19]CCCO2)[C:6]1=O.N>CCO>[F:14][C:10]1[CH:11]=[CH:12][C:13]2[N:5]3[CH2:4][CH2:3][CH2:2][N:1]=[C:6]3[C:7](=[O:19])[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58932574HCID 58932574, compound

Product 1

HCID 58932541HCID 58932541, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
135 °C

Procedure

1′-(3-Aminopropyl)-5′-fluorospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (2.37 g, 8.46 mmol) was dissolved in 2M EtOH.NH3 (200 mL), poured into a steel pressure vessel, and heated at 135° C. for 46 hr. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (97/2/1) followed by a second chromatography eluting with 80/20 Pet ether/acetone to give the title compound as a white solid (1.52 g, 68% yield). Anal. Calc'd for C14H15FN2O2: C, 64.11; H, 5.76; N, 10.68. Found: C, 64.05; H, 5.79; N, 10.61. NMR (300 Mz, DMSO-d6): consistent; MS: (APCI+) m/z 263 [M+H]. m.p.: 130-132° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (97/2/1)
  4. washeluting with 80/20 Pet ether/acetone

Sources & evidence

ORD record
ord-8d8148a963f44e7cae716d730cdae388
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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