Sodium Bicarbonate → HCID 19991716, 화합물

HRID 346062노트

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HRID 346062 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 19991716HCID 19991716, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a0a9f31bd54a412c84580c1bacfee0b6
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059688

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