Hydrochloric Acid → HCID 20041077, compound

HRID 1762459Notes

Reaction equation

HRID 1762459 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[Cl:13]C1C=CC(C2([C:24]#[N:25])CCC2)=CC=1.[BH4-].[Na+].[ClH:28].[CH3:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CCOCC.CC(O)C.O>[ClH:13].[ClH:28].[Cl:28][C:31]1[CH:30]=[CH:29][C:34]([C:11]2([NH:25][CH2:24][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:10][CH2:9][CH2:8]2)=[CH:33][CH:32]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 8058HexaneHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 4311764Sodium borohydrideHCID 178418339Butyllithium

Product 1

HCID 20041077HCID 20041077, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent4×HCID 3776IsopropanolSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2-bromopyridine (12.3 g) in dry ether (80 ml) was added to a 1.55M solution of butyllithium in hexane (30 ml) at -78° C. The mixture was stirred at -78° C. for one hour and a solution of 1-(4-chlorophenyl)cyclobutanecarbonitrile (8 g) in ether (8 ml) added and the temperature of the mixture was allowed to rise to ambient. After one hour a solution of sodium borohydride (3 g) in dry diethyleneglycoldimethyl ether (130 ml) was added and the mixture heated at 95° C. for two hours. Water (100 ml) was added and the mixture extracted with ether. The ether extract was extracted with 8N hydrochloric acid and the acid extract washed with ether, basified with aqueous sodium hydroxide solution and extracted with ether. The ether extract was filtered through diatomaceous earth, dried and the solvent removed by evaporation. The residue was distilled in the range 168°-180° C. at 0.2 mm Hg pressure to yield an oil which was dissolved in ether. Hydrogen chloride gas was passed through the ethereal solution and the resulting precipitate was heated with propan-2-ol to give [1-(4-chlorophenyl)cyclobutyl](pyrid-2-yl)methylamine dihydrochloride (m.p. 240°-245° C. (dec)).

Workup

  1. temperaturethe mixture heated at 95° C. for two hours
  2. extractionthe mixture extracted with ether
  3. extractionThe ether extract
  4. extractionwas extracted with 8N hydrochloric acid
  5. extractionthe acid extract
  6. washwashed with ether
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. filtrationwas filtered through diatomaceous earth
  10. customdried
  11. customthe solvent removed by evaporation
  12. distillationThe residue was distilled in the range 168°-180° C. at 0.2 mm Hg pressure
  13. customto yield an oil which

Sources & evidence

ORD record
ord-cfcdbc57c96140da820e3f26f43ba1f4
Source dataset
uspto-grants-1989_05
Patent number
US04833143

Reaction notes

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