Hydrochloric Acid → HCID 4067151, compound

HRID 2419011Notes

Reaction equation

HRID 2419011 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[C:5]1([C:11]2[CH:16]=[CH:15]C=[CH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:17]=O.Cl.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21].Cl>C(O)C>[CH2:20]([N:22]([CH2:23][CH3:24])[CH2:17][CH2:1][C:2]([C:4]1[CH:13]=[CH:12][C:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:16][CH:15]=1)=[O:3])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 10197650Diethylammonium chlorideHCID 22416343HCID 22416343, compound

Product 1

HCID 4067151HCID 4067151, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 g of biphenyl methyl ketone, 10 g of paraformaldehyde and 30 g of diethylamine hydrochloride were heated under reflux for 6 hours in 200 ml of absolute ethanol and in the presence of 1 ml of 10 N hydrochloric acid. On cooling, a mixture of the reaction product in the form of its hydrochloride and of the initial ketone crystallized from the reaction mixture. These were separated by treating the mixture with 500 ml of 10% hydrochloric acid and the aqueous solution was extracted with ethyl acetate. The organic phase was disposed of and the aqueous phase was made alkaline by the addition of 10 N aqueous soda. The liberated base was finally extracted with ether. After drying the ethereal solution with sodium sulphate and evaporating the ether, 4-(3-diethylamino-1-oxo-propyl)-biphenyl was obtained in the form of a yellow oil and in a yield of 55%.

Workup

  1. temperatureOn cooling
  2. customof the initial ketone crystallized from the reaction mixture
  3. customThese were separated
  4. additionby treating the mixture with 500 ml of 10% hydrochloric acid
  5. extractionthe aqueous solution was extracted with ethyl acetate
  6. additionby the addition of 10 N aqueous soda
  7. extractionThe liberated base was finally extracted with ether
  8. dry with materialAfter drying the ethereal solution with sodium sulphate
  9. customevaporating the ether

Sources & evidence

ORD record
ord-b978f593b5f74ea1bacd8e4999401c15
Source dataset
uspto-grants-1978_08
Patent number
US04104383

Reaction notes

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