Sodium Bicarbonate → HCID 19991716、化合物

HRID 346062ノート

反応式

HRID 346062 の反応式
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

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 14348987HCID 14348987、化合物

生成物 1

HCID 19991716HCID 19991716、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a0a9f31bd54a412c84580c1bacfee0b6
出典データセット
uspto-grants-1991_10
特許番号
US05059688

反応ノート

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