4-Methoxybenzaldehyde → HCID 20225016, compound

HRID 1249166Notes

Reaction equation

HRID 1249166 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([CH:22]([NH2:24])[CH3:23])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[ClH:11].[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][NH:24][CH:22]([C:18]2([C:15]3[CH:14]=[CH:13][C:12]([Cl:11])=[CH:17][CH:16]=3)[CH2:19][CH2:20][CH2:21]2)[CH3:23])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 13083142HCID 13083142, compound

Product 1

HCID 20225016HCID 20225016, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of p-anisaldehyde (6.43 g) and 1-[1-(4-chlorophenyl)cyclobutyl]ethylamine (see Example 1(b) of published British Patent Specification No. 2098602) in the form of its free base (9.09 g) in dry toluene (50 ml) was heated under reflux for 20 hours under nitrogen and water was removed by means of a Dean-Stark apparatus. The reaction mixture was cooled and solid sodium borohydride (4.1 g) was added. Methanol (40 ml) was added dropwise at a temperature of 25°-30° C. The mixture was heated under reflux for one hour and the methanol and toluene removed by evaporation. The residue was cooled to ambient temperature and excess 5N hydrochloric acid added. The mixture was then basified with aqueous sodium hydroxide solution and extracted with ether. The ether extract was washed and shaken with 5N hydrochloric acid to give a white solid which was recrystallised from ethanol to give N-(4-methoxybenzyl)-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 225°-228° C.).

Workup

  1. temperatureunder reflux for 20 hours under nitrogen
  2. customwater was removed by means of a Dean-Stark apparatus
  3. temperatureThe reaction mixture was cooled
  4. additionsolid sodium borohydride (4.1 g) was added
  5. additionMethanol (40 ml) was added dropwise at a temperature of 25°-30° C
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for one hour
  8. customthe methanol and toluene removed by evaporation
  9. additionexcess 5N hydrochloric acid added
  10. extractionextracted with ether
  11. extractionThe ether extract
  12. washwas washed
  13. customto give a white solid which
  14. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-a6b9ce039071446bba01245364e8b638
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

Loading…