Dimethylamine → 2,4-Dichlorophenyl 4'-[(dimethylamino)methyl]-4-biphenylyl ketone hydrochloride

HRID 1645810Notes

Reaction equation

HRID 1645810 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:25][NH:26][CH3:27]>C(O)C>[ClH:23].[CH3:25][N:26]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:27]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 197420972,4-Dichlorophenyl 4'-bromomethyl-4-biphenylyl ketone

Product 1

HCID 198023172,4-Dichlorophenyl 4'-[(dimethylamino)methyl]-4-biphenylyl ketone hydrochlorideYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g of 2,4-dichlorophenyl 4'-bromomethyl-4-biphenylyl ketone and 20 mL of a 33 percent solution of dimethylamine in ethanol were heated to boiling for 4 hours, whereupon the mixture was evaporated. The residue was taken up in ether and treated with an ethereal solution of hydrogen chloride. The precipitated hydrochloride was filtered off and dried. There was obtained 2,4-dichlorophenyl 4'-[(dimethylamino)methyl]-4-biphenylyl ketone hydrochloride with a m.p. of 195°-196° C. Yield 51%.

Workup

  1. customwas evaporated
  2. additiontreated with an ethereal solution of hydrogen chloride
  3. filtrationThe precipitated hydrochloride was filtered off
  4. customdried

Sources & evidence

ORD record
ord-13f89f17495a43a4be2714405a0a1086
Source dataset
uspto-grants-1993_01
Patent number
US05177067

Reaction notes

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