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Formaldehyde → 2-[(4-benzhydryl-1-piperazinyl)methyl]-6-piperidino-3,4-dihydro-1(2H)-naphthalenone

HRID 2050000
Notes
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Reaction equation

HRID 2050000 reaction equation
Cl.[N:2]1([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12][CH2:11]3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[CH:20]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C=O.[C:41](=O)([O-])O.[Na+]>C(O)C>[CH:20]([N:33]1[CH2:38][CH2:37][N:36]([CH2:41][CH:13]2[CH2:12][CH2:11][C:10]3[C:15](=[CH:16][CH:17]=[C:8]([N:2]4[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]4)[CH:9]=3)[C:14]2=[O:18])[CH2:35][CH2:34]1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 203431836-piperidino-3,4-dihydro-1(2H)-naphthalenone hydrochlorideHCID 441468911-Benzhydrylpiperazinium chloride

Product 1

HCID 203431882-[(4-benzhydryl-1-piperazinyl)methyl]-6-piperidino-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml. of ethanol was dissolved a mixture of 2 g. of 6-piperidino-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 aqueous sodium hydrogen carbonate and extracted with chloroform. The extract was dried and the solvent was distilled off under reduced pressure, whereby 2-[(4-benzhydryl-1-piperazinyl)methyl]-6-piperidino-3,4-dihydro-1(2H)-naphthalenone was obtained as an oil. This oil was dissolved in 50 ml. of methanol and the solution was 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 chloroform. The extract was dried and the solvent was distilled off under reduced pressure. By the above procedure there was obtained 2-[(4-benzhydryl-1-piperazinyl)methyl]-6-piperidino-1,2,3,4-tetrahydro-1-naphthalenol as an oil. This oily product was dissolved in 50 ml. of 20% ethanolic HCl and the solution was heated under reflux for 2 hours. After cooling, the crystals were collected by filtration, whereby 2.7 g. of 3-[(4-benzhydryl-1-piperazinyl)methyl]-7-piperidino-1,2-dihydronaphthalene hydrochloride was obtained as colorless prisms melting at 195°-199° C.(decomposition).

Workup

  1. additiona mixture of 2 g
  2. extractionextracted with chloroform
  3. customThe extract was dried
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4197083e8dc74b209b340d2ecc9736f1
Source dataset
uspto-grants-1980_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04199582

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes