Diethyl Ether → HCID 13279976, compound

HRID 1249170Notes

Reaction equation

HRID 1249170 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH:17]([NH2:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[CH2:25]([N:27](CC)[CH2:28][CH3:29])[CH3:26].CC[O:34]CC>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2([CH:17]([NH:24][C:3](=[O:4])[CH2:2][N:27]3[CH2:28][CH2:29][O:34][CH2:26][CH2:25]3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:16][CH2:15][CH2:14]2)=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 13083225HCID 13083225, compound

Product 1

HCID 13279976HCID 13279976, compound

Procedure

A solution of chloroacetylchloride (5.5 g) in dry ether (30 ml) was added dropwise to a solution of α-[1-(4-chlorophenyl)cyclobutyl]benzylamine (see Example 16 of published British Patent Specification No. 2098602) in the form of its free base (11.95 g) and a solution of triethylamine (4.9 g) in dry ether (40 ml) at around 5° C. The mixture was stirred at room temperature for twenty hours and then filtered. The filtrate was washed with water, aqueous sodium bicarbonate solution and water and dried over magnesium sulphate. Morpholine (8.4 g) was added and the mixture heated under reflux for 24 hours. The reaction mixture was extracted with 2N hydrochloric acid and the aqueous fraction washed with ether. Addition of aqueous sodium hydroxide precipitated a solid which was recrystallised from petroleum ether (b.p. 80°-100° C.) to give N-{α-[1-(4-chlorophenyl)cyclobutyl]benzyl}-2-morpholinoacetamide (m.p. 95°-97° C.).

Workup

  1. customat around 5° C
  2. filtrationfiltered
  3. washThe filtrate was washed with water, aqueous sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulphate
  5. additionMorpholine (8.4 g) was added
  6. temperaturethe mixture heated
  7. temperatureunder reflux for 24 hours
  8. extractionThe reaction mixture was extracted with 2N hydrochloric acid
  9. washthe aqueous fraction washed with ether
  10. additionAddition of aqueous sodium hydroxide
  11. customprecipitated a solid which
  12. customwas recrystallised from petroleum ether (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-0798253a76644747ac42be9c5121ea81
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

Loading…