Formaldehyde → 2-[(4-Benzhydryl-1-piperazinyl)methyl]-6-morpholino-1,2,3,4-tetrahydro-1-naphthalenol

HRID 2049998ノート

反応式

HRID 2049998 の反応式
Cl.O1CCN(C2C=C3C(=CC=2)C(=O)CCC3)CC1.Cl.C(N1CCNCC1)(C1C=CC=CC=1)C1C=CC=CC=1.C=O.C(=O)([O-])O.[Na+].[CH:46]([N:59]1[CH2:64][CH2:63][N:62]([CH2:65][CH:66]2[CH2:75][CH2:74][C:73]3[C:68](=[CH:69][CH:70]=[C:71]([N:76]4[CH2:81][CH2:80][O:79][CH2:78][CH2:77]4)[CH:72]=3)[C:67]2=[O:82])[CH2:61][CH2:60]1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[BH4-].[Na+]>CO.C(O)C>[CH:46]([N:59]1[CH2:60][CH2:61][N:62]([CH2:65][CH:66]2[CH2:75][CH2:74][C:73]3[C:68](=[CH:69][CH:70]=[C:71]([N:76]4[CH2:81][CH2:80][O:79][CH2:78][CH2:77]4)[CH:72]=3)[CH:67]2[OH:82])[CH2:63][CH2:64]1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

参加物

9

反応物 6

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 203431782-[(4-benzhydryl-1-piperazinyl)methyl]-6-morpholino-3,4-dihydro-1(2H)-naphthalenoneHCID 203431796-morpholino-3,4-dihydro-1(2H)-naphthalenone hydrochlorideHCID 441468911-Benzhydrylpiperazinium chloride

生成物 1

HCID 131795422-[(4-Benzhydryl-1-piperazinyl)methyl]-6-morpholino-1,2,3,4-tetrahydro-1-naphthalenol

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

In 50 ml. of ethanol was dissolved a mixture of 2 g. of 6-morpholino-3,4-dihydro-1(2H)-naphthalenone hydrochloride, 4 g. of 1-benzhydrylpiperazine hydrochloride and 4 g. of a 37% aqueous solution of formalin. The solution was allowed to stand at room temperature for 10 days, after which it was neutralized with an aqueous solution of sodium hydrogen carbonate and extracted with 100 ml. of chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. By the above procedure there was obtained 5 g. of 2-[(4-benzhydryl-1-piperazinyl)methyl]-6-morpholino-3,4-dihydro-1(2H)-naphthalenone as colorless oil. IRνc=o neat 1665 cm-1. This oil was dissolved in 50 ml. of methanol and stirred with 3 g. of sodium borohydride at room temperature for 30 minutes. The reaction mixture was diluted with 500 ml. of water and extracted with 150 ml. of chloroform. The extract was dried and distilled under reduced pressure to remove the solvent, whereupon 4.5 g. of 2-[(4-benzhydryl-1-piperazinyl)methyl]-6-morpholino-1,2,3,4-tetrahydro-1-naphthalenol was obtained as an oil. A portion of this oil was purified by chromatography on a column of silica gel and lead to its fumarate melting at 184°-187° C.(decomposition).

後処理

  1. additiona mixture of 2 g
  2. extractionextracted with 100 ml
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customBy the above procedure there was obtained 5 g
  6. dissolutionThis oil was dissolved in 50 ml
  7. additionThe reaction mixture was diluted with 500 ml
  8. extractionof water and extracted with 150 ml
  9. customThe extract was dried
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent

出典と根拠

ORDレコード
ord-26d58f603c2c4b0eb37625ee4be2dee9
出典データセット
uspto-grants-1980_04
特許番号
US04199582

反応ノート

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