Hydrochloric Acid → HCID 13083341, compound

HRID 325878Notes

Reaction equation

HRID 325878 reaction equation
FC(F)(F)C(O)=O.[BH4-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([CH2:22][C:23](=[N:26]O)[CH2:24][CH3:25])[CH2:21][CH2:20][CH2:19]2)[CH:14]=[CH:15][C:16]=1[Cl:17].[OH-].[Na+].Cl>O1CCCC1.CCOCC.O>[ClH:10].[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([CH2:22][CH:23]([NH2:26])[CH2:24][CH3:25])[CH2:21][CH2:20][CH2:19]2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 73165579HCID 73165579, compound

Product 1

HCID 13083341HCID 13083341, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of trifluoroacetic acid (2.33 ml) in tetrahydrofuran (5 ml) was added to a stirred suspension of sodium borohydride (1.13 g) in tetrahydrofuran (30 ml) over a period of five minutes. A solution of the oxime (1.7 g) prepared as described above in tetrahydrofuran (25 ml) was added dropwise and the mixture heated under reflux for six hours. The mixture was cooled and water (25 ml) and then 5 N sodium hydroxide solution (25 ml) were added. The mixture was extracted with ether and the extract washed with water, dried and evaporated to give a residue which was dissolved in petroleum ether (25 ml). Dry hydrogen chloride gas was passed through the ether solution to give 1-{[1-(3,4-dichlorophenyl)cyclobutyl]methyl}propylamine hydrochloride (m.p. 222°-224° C.). (Formula I R1, R2, R3 and R4 =H; R5 =4-Cl; R6 =3-Cl; R7 =Et and R8 =H).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture heated
  3. temperatureunder reflux for six hours
  4. temperatureThe mixture was cooled
  5. extractionThe mixture was extracted with ether
  6. washthe extract washed with water
  7. customdried
  8. customevaporated
  9. customto give a residue which

Sources & evidence

ORD record
ord-e2b97a0bbd0e4c9f8d162af0419491ac
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

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