Dimethylamine → HCID 19761029, compound

HRID 249275Notes

Reaction equation

HRID 249275 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][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.[CH3:22][NH:23][CH3:24].O>C(O)C>[CH3:22][N:23]([CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][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

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 19761051HCID 19761051, compound

Product 1

HCID 19761029HCID 19761029, compoundYield 97%

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-db7f8615aef84cbab44aac075df86300
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Reaction notes

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