Sodium Bicarbonate → HCID 19991716, compound

HRID 346062Notes

Reaction equation

HRID 346062 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.[ClH:29].[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][Cl:34].C(=O)(O)[O-].[Na+]>CN(C=O)C>[ClH:34].[ClH:29].[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][N:16]1[CH:15]=[C:14]([O:13][C:12]2[CH:25]=[CH:26][C:9]([C:8]([F:7])([F:27])[F:28])=[CH:10][CH:11]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[CH:17]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 14348987HCID 14348987, compound

Product 1

HCID 19991716HCID 19991716, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 1 (8.5 g, 0.028 mole), 2-dimethylaminoethyl chloride hydrochloride (6.5 g, 0.045 mole) and sodium bicarbonate (18 g, 0.021 mole) in DMF (125 ml) was stirred at 60° C. for two hours. The reaction mixture was concentrated to a slurry which was stirred with water and extracted with ethyl acetate-ether. The organic extracts were washed twice with water and dried (saturated NaCl, anhydrous MgSO4). The solution was filtered and concentrated to an oil (8 g) which was converted to the dihydrochloride salt (6 g, 48% d 170° C.) by the addition of ethereal HCl. This material was recrystallized twice from a 20:1 ethyl acetate/methanol solution to yield 3-(2-dimethylaminoethyl)-1-(p-trifluoromethylphenoxy)-3-benzazepine dihydrochloride, d 137°-238° C.

Workup

  1. concentrationThe reaction mixture was concentrated to a slurry which
  2. stirringwas stirred with water
  3. extractionextracted with ethyl acetate-ether
  4. washThe organic extracts were washed twice with water
  5. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  6. filtrationThe solution was filtered
  7. concentrationconcentrated to an oil (8 g) which
  8. additionwas converted to the dihydrochloride salt (6 g, 48% d 170° C.) by the addition of ethereal HCl
  9. customThis material was recrystallized twice from a 20:1 ethyl acetate/methanol solution

Sources & evidence

ORD record
ord-a0a9f31bd54a412c84580c1bacfee0b6
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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