Formaldehyde → HCID 20343182, compound

HRID 2049999Notes

Reaction equation

HRID 2049999 reaction equation
Cl.[CH3:2][N:3]([CH3:15])[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8][CH2:7]2.Cl.[CH:17]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C=O.[C:38](=O)([O-])O.[Na+]>O.C(O)C>[CH:17]([N:30]1[CH2:35][CH2:34][N:33]([CH2:38][CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([N:3]([CH3:15])[CH3:2])[CH:5]=3)[C:10]2=[O:14])[CH2:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 203431746-(Dimethylamino)-3,4-dihydronaphthalen-1(2H)-one--hydrogen chloride (1/1)HCID 441468911-Benzhydrylpiperazinium chloride

Product 1

HCID 20343182HCID 20343182, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 100 ml. of ethanol was dissolved 2 g. of 6-dimethylamino-3,4-dihydro-1(2H)-naphthalenone hydrochloride, 4 g. of 1-benzhydrylpiperazine hydrochloride and 4 g. of a 37% aqueous solution of formalin and the reaction was carried out at room temperature for 2 hours. The reaction mixture was diluted with 500 ml. of water, neutralized with sodium hydrogen carbonate and extracted with chloroform. The chloroform extract was dried and distilled under reduced pressure to remove the solvent, whereupon 2-[(4-benzhydryl-1-piperazinyl)methyl]-6-dimethylamino-3,4-dihydro-1(2H)-naphthalenone was obtained as an oil. This oily product was dissolved in 50 ml. of methanol and stirred with 2.5 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-dimethylamino-1,2,3,4-tetrahydro-1-naphthalenol as an oil. This oil was dissolved in 50 ml. of ethanolic HCl and the solution was heated under reflux for 2 hours. Upon cooling there was obtained 1.5 g. of 3-[(4-benzhydryl-1-piperazinyl)methyl]-7-dimethylamino-1,2-dihydronaphthalene hydrochloride as colorless needles melting at 190°-195° C.(decomposition).

Workup

  1. additionThe reaction mixture was diluted with 500 ml
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. customwas dried
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-4af19a55f154460bb475535e35d8cbac
Source dataset
uspto-grants-1980_04
Patent number
US04199582

Reaction notes

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