Hydrochloric Acid → HCID 131717790, compound

HRID 273817Notes

Reaction equation

HRID 273817 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH2:12].[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)=[O:19].C(=O)(O)[O-].[Na+].[I-].[K+].Cl>CN(C)C=O.C(O)C>[ClH:13].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH:12][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=1)=[O:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 150532-Aminomethyl-1,4-benzodioxaneHCID 516892Sodium Bicarbonate2×HCID 15229344HCID 15229344, compound

Product 1

HCID 131717790HCID 131717790, compoundYield 12.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydro-1,4-benzodioxin-2-methanamine (350 mg) and 5-chloro-N-[4-(trifluoromethyl)phenyl]-pentanamide (593 mg) were stirred in dimethylformamide (7.0 mL) under a nitrogen atmosphere. Sodium bicarbonate (395 mg) and potassium iodide (40 mg) were added and mixture was stirred for 60 hours at 70°-75° C. Saturated sodium bicarbonate solution (50 mL) was added to the cooled reaction and the mixture extracted with diethyl ether (3×30 mL). The combined extracts were dried (MgSO4), filtered, and concentrated in vacuo. The resulting oil was chromatographed eluting with 40:60 ethyl acetate:hexane, then 10:90 ethanol:ethyl acetate to give a yellow-white solid with an Rf of 0.15 in 50:50 ethyl acetate:ethanol. This solid was dissolved in ethanol (20 mL) and treated with 1.0M aqueous HCl (1.0 mL). The solution was concentrated in vacuo to a white solid which after recrystallization from ethanol:ethyl acetate afforded the title compound as a white powder (117 mg).

Workup

  1. extractionthe mixture extracted with diethyl ether (3×30 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was chromatographed
  6. washeluting with 40:60 ethyl acetate
  7. customhexane, then 10:90 ethanol:ethyl acetate to give a yellow-white solid with an Rf of 0.15 in 50:50 ethyl acetate
  8. concentrationThe solution was concentrated in vacuo to a white solid which
  9. customafter recrystallization from ethanol

Sources & evidence

ORD record
ord-6280104f02a1452983f96b57c34dbb91
Source dataset
uspto-grants-1995_02
Patent number
US05387604

Reaction notes

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