Hydrochloric Acid → HCID 20225042, compound

HRID 1249164Notes

Reaction equation

HRID 1249164 reaction equation
[C:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].Cl.[NH2:17][CH2:18][C:19]([NH2:21])=[O:20].C([BH3-])#N.[Na+].Cl.C(O)(=O)/C=C\C(O)=O>CO.CCOCC.CC(C)=O.O>[ClH:14].[Cl:15][C:10]1[CH:9]=[C:8]([C:4]2([CH:1]([NH:17][CH2:18][C:19]([NH2:21])=[O:20])[CH3:2])[CH2:7][CH2:6][CH2:5]2)[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 444266Maleic AcidHCID 2723639Glycinamide hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 130831391-Acetyl-1-(3,4-dichlorophenyl)cyclobutane

Product 1

HCID 20225042HCID 20225042, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A mixture of 1-acetyl-1-(3,4-dichlorophenyl)cyclobutane (2.43 g), glycinamide hydrochloride (2.21 g) powdered potassium hydroxide (1.2 g) and sodium cyanoborohydride (1.5 g) in methanol (20 ml) was stirred at 0°-5° C. for 2 hours then for a total of 10 days at ambient temperature. The mixture was cooled and 5N hydrochloric acid added. The mixture was then basified, extracted into ether, washed with water, dried and evaporated to give an oil. This oil was dissolved in ether and a solution of maleic acid (1.0 g) in dry ether (100 ml) was added to give an oil which was dissolved in acetone. Ether was then added to give a white solid which was dissolved in water, basified and extracted into ether. Passing hydrogen chloride gas through the dried ethereal extract gave 2-{1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamino}acetamide hydrochloride (m.p. 240°-245° C.).

Workup

  1. customfor a total of 10 days
  2. customat ambient temperature
  3. temperatureThe mixture was cooled
  4. extractionextracted into ether
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. customto give an oil which
  10. customto give a white solid which
  11. extractionextracted into ether
  12. extractionPassing hydrogen chloride gas through the dried ethereal extract

Sources & evidence

ORD record
ord-65504fee27c14af48d7d367b1a42a84d
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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