Hydrochloric Acid → HCID 19823772, compound

HRID 1650959Notes

Reaction equation

HRID 1650959 reaction equation
C(OC([O:6][CH2:7][CH2:8][CH2:9][Li])C)C.[Cl:11][C:12]1[CH:13]=[C:14]([C:19]2([C:23]#[N:24])[CH2:22][CH2:21][CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18].[BH4-].[Na+].Cl>CCOCC.CC(O)C.O>[ClH:11].[NH2:24][CH:23]([C:19]1([C:14]2[CH:15]=[CH:16][C:17]([Cl:18])=[C:12]([Cl:11])[CH:13]=2)[CH2:20][CH2:21][CH2:22]1)[CH2:9][CH2:8][CH2:7][OH:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178506874HCID 178506874, compound

Product 1

HCID 19823772HCID 19823772, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent2×

Procedure

A 0.25M solution of 3-[1-(ethoxy)ethoxy]propyllithium [prepared from 3-[1-(ethoxy)ethoxy]propyl bromide (20 g), lithium strips (1.6 g) and ether (75 ml)] was added to a solution of 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile (4.44 g) in dry ether (100 ml) at 0° C. under argon. The mixture was stirred for 16 hours at ambient temperature and propan-2-ol (50 ml) and then a solution of sodium borohydride (1.5 g) in propan-2-ol (60 ml) were added and the mixture stirred at ambient temperature for 2 days and then heated under reflux for 21/2 hours. The mixture was cooled, poured into water (500 ml) and excess concentrated hydrochloric acid was added. The mixture was heated at 90°-95° C. for one hour, cooled, basified and extracted with ether. The extract was dried and evaporated to given an oil which was treated with a further mixture of sodium borohydride (1 g) and propan-2-ol (50 ml) at reflux for 41/2 hours. The mixture was cooled, and water was added and the resulting mixture extracted with ether. The extract was dried, and evaporated to give an oil which was distilled (170° C./0.65-0.25 mm Hg). The distillate was dissolved in propan-2-ol, 5N-hydrochloric acid was added and the solution evaporated to dryness. The residue was dried by azeotropic distillation with propan-2-ol to give a solid which was triturated with propan-2-ol to give 4-amino-4-[1-(3,4-dichlorophenyl)cyclobutyl]butan-1-ol hydrochloride (m.p. 211° C. (dec)-shrinks 203° C.).

Workup

  1. stirringthe mixture stirred at ambient temperature for 2 days
  2. temperatureheated
  3. temperatureunder reflux for 21/2 hours
  4. temperatureThe mixture was cooled
  5. additionwas added
  6. temperatureThe mixture was heated at 90°-95° C. for one hour
  7. temperaturecooled
  8. extractionextracted with ether
  9. customThe extract was dried
  10. customevaporated
  11. additionwas treated with a further mixture of sodium borohydride (1 g) and propan-2-ol (50 ml)
  12. temperatureat reflux for 41/2 hours
  13. temperatureThe mixture was cooled
  14. additionwater was added
  15. extractionthe resulting mixture extracted with ether
  16. customThe extract was dried
  17. customevaporated
  18. customto give an oil which
  19. distillationwas distilled (170° C./0.65-0.25 mm Hg)
  20. dissolutionThe distillate was dissolved in propan-2-ol
  21. addition5N-hydrochloric acid was added
  22. customthe solution evaporated to dryness
  23. dry with materialThe residue was dried by azeotropic distillation with propan-2-ol
  24. customto give a solid which
  25. customwas triturated with propan-2-ol

Sources & evidence

ORD record
ord-8e040846b7be47c2b5b192d6d0c3b8bc
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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