Hydrochloric Acid → HCID 21862775, compound

HRID 856835Notes

Reaction equation

HRID 856835 reaction equation
N1([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)CCCCC1.C(OCC)(=O)C1C(=CC=CC=1)C(OCC)=[O:19].C(N(CC)CC)C.[F:38][C:39]1[CH:48]=[CH:47][C:42]([C:43](=[O:46])[CH2:44]Br)=[CH:41][CH:40]=1.Cl>O1CCCC1>[F:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([CH2:44][CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[O:19])=[O:46])=[CH:41][CH:40]=1

Participants

6

Procedure

4.68 g of the β-piperidinostyrene/diethyl phthalate mixture were dissolved in 70 ml of anhydrous tetrahydrofuran, and 1.01 g (10 mmol) of triethylamine were added to the resulting solution. 2.60 g (12 mmol) of 4-fluorophenacyl bromide were then added to the resulting mixture, which was then stirred at room temperature for 3 hours. At the end of this time, 30 ml of 1N aqueous hydrochloric acid were added to the reaction mixture, and the mixture was stirred at room temperature for a further 1 hour. It was then extracted with diethyl ether. The organic extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure and the residue was applied to a silica gel chromatography column and eluted with a 95:5 by volume mixture of hexane and ethyl acetate, to give 0.50 g of the title compound as a slightly yellow oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for a further 1 hour
  2. extractionIt was then extracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. washeluted with a 95:5 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-306f56b6a7ca449392d3093c9bd73999
Source dataset
uspto-grants-2006_12
Patent number
USRE039420E1

Reaction notes

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