Hydrochloric Acid → HCID 3030533, compound

HRID 2397631Notes

Reaction equation

HRID 2397631 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9](O)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8](C(=O)C2C=CC=CC=2)[CH2:7]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 21436111HCID 21436111, compound

Product 1

HCID 3030533HCID 3030533, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

30 g. of 1-(3-methoxypropyl)-3-benzoyl-4-hydroxy-4-phenylpiperidine are suspended in 225 ml. of anhydrous benzene. 50 g. of finely pulverized, anhydrous aluminum chloride are added thereto within 20 minutes, while stirring. The reaction temperature increases during said addition up to 60° C. The reaction mixture is then kept at from 50° to 55° C. for about 1 hour, is cooled to room temperature, and is added to a mixture of ice and concentrated hydrochloric acid. The benzene layer is separated from the aqueous layer by means of a separating funnel and is washed once with dilute hydrochloric acid. The combined aqueous layers are rendered alkaline by the addition of 40% sodium hydroxide solution. The precipitated base is separated by repeated extraction with ether. The combined ether extracts are dried over anhydrous potassium carbonate and the ether is distilled off. 21 g. of the crude base remain as residue. On distillation in a high vacuum, pure 1-(3-methoxypropyl)-4,4-diphenylpiperidine is obtained in the form of a light oil boiling at 130° C./0.01 mm. Hg.

Workup

  1. temperatureThe reaction temperature increases
  2. additionaddition up to 60° C
  3. waitThe reaction mixture is then kept at from 50° to 55° C. for about 1 hour
  4. customThe benzene layer is separated from the aqueous layer by means of a separating funnel
  5. washis washed once with dilute hydrochloric acid
  6. additionby the addition of 40% sodium hydroxide solution
  7. customThe precipitated base is separated
  8. extractionextraction with ether
  9. dry with materialThe combined ether extracts are dried over anhydrous potassium carbonate
  10. distillationthe ether is distilled off
  11. distillationOn distillation in a high vacuum

Sources & evidence

ORD record
ord-dacf1623fc584c1eb0aa4459212199ea
Source dataset
uspto-grants-1977_05
Patent number
US04022786

Reaction notes

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