Formaldehyde → 2-(4-benzhydryl-1-piperazinylmethyl)-6,7-dimethoxy-3,4-dihydro-1(2H)-naphthalenone

HRID 26190Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]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(OCC)C.C(O)C>[CH:17]([N:30]1[CH2:35][CH2:34][N:33]([CH2:38][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]2=[O:15])[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

Conditions

Temperature: 80 °C

Procedure

In 100 ml. of ethanol is dissolved a mixture of 5 g. of 6,7-dimethoxy-3,4-dihydro-1(2H)-naphthalenone, 8 g. of 1-benzhydrylpiperazine hydrochloride and 10 g. of 37% aqueous formalin and the solution is allowed to stand at room temperature overnight, after which time it is heated at 80° C. for 7 hours. To the 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 and distilled under reduced pressure. To the oily residue is added methanol, whereupon 5 g. of 2-(4-benzhydryl-1-piperazinylmethyl)-6,7-dimethoxy-3,4-dihydro-1(2H)-naphthalenone is obtained as colorless crystals melting at 142°-144° C.

Workup

additiona mixture of 5 g
additionTo the reaction mixture is added 500 ml
extractionextracted with chloroform
customThe extract is dried
distillationdistilled under reduced pressure
additionTo the oily residue is added methanol

Sources & evidence

ORD record: ord-4bf36a752f8c4cf89b8af9f30c002927
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148897

Reaction notes

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