Formaldehyde → 2-(4-benzhydryl-1-piperazinylmethyl)-3,4-dihydro-1(2H)-naphthalenone

HRID 26191

반응식

HRID 26191 반응식
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl.[CH:13]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C=O.[C:34](=O)([O-])O.[Na+]>O.C(OCC)C.C(O)C>[CH:13]([N:26]1[CH2:31][CH2:30][N:29]([CH2:34][CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]2=[O:11])[CH2:28][CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

8

반응물 4

HCID 712FormaldehydeHCID 107241-TetraloneHCID 516892Sodium BicarbonateHCID 441468911-Benzhydrylpiperazinium chloride

생성물 1

HCID 213250002-(4-benzhydryl-1-piperazinylmethyl)-3,4-dihydro-1(2H)-naphthalenone

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 3283Diethyl Ether용매

반응 조건

온도
80 °C

실험 절차

In 100 ml. of ethanol is dissolved a mixture of 10 g. of 3,4-dihydro-1(2H)-naphthalenone, 22 g. of 1-benzhydrylpiperazine hydrochloride and 10 g. of 37% aqueous formalin and the mixed solution is stirred at room temperature for 3 hours and, then, heated at 80° C. for another 3 hours. To this reaction mixture is added 500 ml. of water and, after shaking with 100 ml. of diethyl ether, the water layer is neutralized with sodium hydrogen carbonate and extracted with chloroform. The extract is dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. By the above procedure is obtained an oil of 2-(4-benzhydryl-1-piperazinylmethyl)-3,4-dihydro-1(2H)-naphthalenone. This product is dissolved in a mixture of 50 ml. of chloroform and 100 ml. of methanol. After addition of 5 g. of sodium borohydride, the mixture is stirred at room temperature for 30 minutes. Following addition of 500 ml. of water, the reaction mixture is extracted with chloroform and the extract is dried. The solvent is distilled off under reduced pressure and the residue is purified by chromatography on a column of silica gel (acetone-benzene=1:9). By the above procedure is obtained 4.3 g. of 2-(4-benzhydryl-1-piperazinylmethyl)-1,2,3,4-tetrahydro-1-naphthalenol as colorless prisms melting at 179°-181° C.

후처리

  1. additiona mixture of 10 g
  2. additionTo this reaction mixture is added 500 ml
  3. extractionextracted with chloroform
  4. dry with materialThe extract is dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent

출처 및 근거

ORD 기록
ord-5d57ef2d0a3e4f38aa7a8a128ac0839b
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04148897

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