Sodium amide → HCID 70605177, compound

HRID 1390940Notes

Reaction equation

HRID 1390940 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:4][CH:3]=1.[CH2:26]([N:28]([CH2:33][CH3:34])[CH:29]([Cl:32])[CH2:30][CH3:31])[CH3:27].[NH2-].[Na+]>C1(C)C=CC=CC=1>[ClH:32].[CH2:26]([N:28]([CH2:29][CH2:30][CH2:31][O:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([CH3:25])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:4][CH:3]=1)[CH2:33][CH3:34])[CH3:27]

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 18504944HCID 18504944, compoundHCID 54021829HCID 54021829, compound

Product 1

HCID 70605177HCID 70605177, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

Fifty-three grams of 4-hydroxy-3,5-dimethyl-β,β-diphenylpropiophenone (prepared as in Example 5) are dissolved in 300 mls of dry toluene. Thirty-eight and four-tenths grams (100% excess) of 1-diethylamino-propylchloride, dissolved in 100 mls of toluene, are added to this solution dropwise. At that time, 13.8 grams sodium amide, 50% in toluene suspension, are added dropwise with stirring. This mixture is boiled for two days under reflux. The precipitate is filtered and the toluene is evaporated in vacuo. The residue is taken up in ether and washed several times with water. After drying with sodium sulfate, the hydrochloride is precipitated with ethereal hydrochloric acid and it is filtered over active carbon and recrystallized from acetone/ether. 4-[3-(N,N-diethylamino)-propoxy]-3,5-dimethyl-β,β-diphenylpropiophenone hydrochloride (Melting point = 179° C.) is obtained.

Workup

  1. additionare added to this solution dropwise
  2. temperatureunder reflux
  3. filtrationThe precipitate is filtered
  4. customthe toluene is evaporated in vacuo
  5. washwashed several times with water
  6. dry with materialAfter drying with sodium sulfate
  7. customthe hydrochloride is precipitated with ethereal hydrochloric acid and it
  8. filtrationis filtered over active carbon
  9. customrecrystallized from acetone/ether

Sources & evidence

ORD record
ord-ae03fa3f77444ea2806af450c729a503
Source dataset
uspto-grants-1979_02
Patent number
US04140770

Reaction notes

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