Hydrochloric Acid → HCID 20301091, compound

HRID 1733282Notes

Reaction equation

HRID 1733282 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[CH2:3][CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[ClH:18].[CH3:19][NH:20][CH3:21].[CH2:22]=O.Cl>CC(O)C>[ClH:18].[CH3:19][N:20]([CH2:22][CH:3]1[C:4](=[O:5])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:1][CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10251FlavanoneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 20301091HCID 20301091, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 44.8 g (0.2 mol) of flavanone (commercially available from Aldrich Chemical Co., Milwaukee, Wisconsin), 32.6 g (0.4 mole) of dimethylamine hydrochloride, 12.6 g (0.4 mol) of paraformaldehyde, 1 ml of concentrated HCl, and 120 ml of 2-propanol was stirred at reflux for 1 hour. The reaction was then allowed to cool to room temperature, the solvent was removed under reduced pressure and the residue partitioned between 400 ml of ether and 1 liter of 5 percent aqueous hydrochloric acid. The aqueous phase was separated, washed with 200 ml of ether, cooled and made basic with solid K2CO3. The liberated base was extracted into ether, the ether solution dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was taken up in 200 ml of ethyl acetate and treated with excess acetyl chloride and ethanol. Upon cooling, white crystals precipitated. After drying, a yield of 43.8 g of 3-dimethylaminomethyl flavanone hydrochloride, (mp 172°-174° C.) was obtained.

Workup

  1. temperatureat reflux for 1 hour
  2. customthe solvent was removed under reduced pressure
  3. customthe residue partitioned between 400 ml of ether and 1 liter of 5 percent aqueous hydrochloric acid
  4. customThe aqueous phase was separated
  5. washwashed with 200 ml of ether
  6. temperaturecooled
  7. extractionThe liberated base was extracted into ether
  8. dry with materialthe ether solution dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. additiontreated with excess acetyl chloride and ethanol
  12. temperatureUpon cooling
  13. customwhite crystals precipitated
  14. customAfter drying

Sources & evidence

ORD record
ord-df67ed9e977c4b36a76ddcc14ff11808
Source dataset
uspto-grants-1980_12
Patent number
US04241069

Reaction notes

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