Hydrochloric Acid → HCID 19823772, compound

HRID 728281Notes

Reaction equation

HRID 728281 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 borohydride2×HCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178506874HCID 178506874, compound

Product 1

HCID 19823772HCID 19823772, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent3×

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 give 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. customto give an oil which
  12. temperatureat reflux for 41/2 hours
  13. temperatureThe mixture was cooled
  14. extractionthe resulting mixture extracted with ether
  15. customThe extract was dried
  16. customevaporated
  17. customto give an oil which
  18. distillationwas distilled (170° C./0.65-0.25 mm Hg)
  19. dissolutionThe distillate was dissolved in propan-2-ol
  20. addition5N-hydrochloric acid was added
  21. customthe solution evaporated to dryness
  22. dry with materialThe residue was dried by azeotropic distillation with propan-2-ol
  23. customto give a solid which
  24. customwas triturated with propan-2-ol

Sources & evidence

ORD record
ord-4fcc39e74abc4932b276cea9248adfb9
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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