Dimethylamine → Benzophenone

HRID 1030667Notes

Reaction equation

HRID 1030667 reaction equation
BrCCCCCO[C:8]1[CH:21]=[CH:20][C:11]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1.CNC.O>C(O)C>[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[C:11]1[CH:20]=[CH:21][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 19761051HCID 19761051, compound

Product 1

HCID 3102Benzophenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3.0 g of 4-[(5-bromopentyl)oxy]benzophenone in 30 ml of ethanol was heated to 90° in a pressure tube for 1.5 hours with 16 ml of a 33 percent solution of dimethylamine in ethanol. After cooling the mixture was poured into water and extracted three times with ethyl acetate. The organic phases, dried over sodium sulphate, were evaporated and the residue was chromatographed on neutral aluminium oxide (activity grade III) with hexane:ethyl acetate 7:3). There were obtained 2.69 g (97%) of 4- (5-(dimethylamino)pentyl)oxy]benzophenone as a colorless oil.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic phases, dried over sodium sulphate
  4. customwere evaporated
  5. customthe residue was chromatographed on neutral aluminium oxide (activity grade III) with hexane:ethyl acetate 7:3)

Sources & evidence

ORD record
ord-5783fedc3381435b81fb331541b40847
Source dataset
uspto-grants-1992_04
Patent number
US05106878

Reaction notes

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