Hydrochloric Acid → HCID 20041069, compound

HRID 1762461Notes

Reaction equation

HRID 1762461 reaction equation
CN1C=CC=N1.C([Li])CCC.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2(C#N)[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.ClC1C=CC(C2([C:36]([C:38]3[N:42]([CH3:43])[N:41]=[CH:40][CH:39]=3)=[NH:37])CCC2)=CC=1.[BH4-].[Na+].Cl>CCCCCC.CCOCC.O>[ClH:12].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2([NH:37][CH2:36][C:38]3[N:42]([CH3:43])[N:41]=[CH:40][CH:39]=3)[CH2:20][CH2:21][CH2:22]2)=[CH:17][CH:18]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 702551H-Pyrazole, 1-methyl-HCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 4311764Sodium borohydrideHCID 20041033HCID 20041033, compoundHCID 178418339Butyllithium

Product 1

HCID 20041069HCID 20041069, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

1-Methylpyrazole (4.8 g) was added to a mixture of dry ether (60 ml) and a 1.7M solution of butyllithium in hexane (30 ml) under nitrogen at a temperature of less than 5° C. N,N,N'N'-Tetramethylethylenediamine (TMEDA) (8.3 g) was added and the mixture stirred at 0°-5° C. for one and three quarter hours and then 1-(4-chlorophenyl)cyclobutanecarbonitrile (6.0 g) was added and the mixture stirred for 90 minutes at a temperature in the range 0 to 5° C. Water was added and the reaction mixture extracted with ether. The extract was washed, dried and evaporated to give an oil which is [1-(4-chlorophenyl)cyclobutyl](1-methylpyrazol-5yl)methanimine. The imine was stirred with a mixture of sodium borohydride (2 g) in diethyleneglycoldimethyl ether (100 ml) under nitrogen at 95° C. for two hours. The mixture was poured into water and extracted with ether. The extract was washed, dried and evaporated to give a residue which was dissolved in dry ether. Hydrogen chloride gas was passed through the ethereal solution to give a hydrochloride salt of [1-(4-chlorophenyl)cyclobutyl](1-methylpyrazol-5-yl)methylamine hydrochloride (m.p. 316°-318° C.) containing 1.25 moles of hydrochloride and 0.25 moles of water.

Workup

  1. customat a temperature of less than 5° C
  2. stirringthe mixture stirred for 90 minutes at a temperature in the range 0 to 5° C
  3. extractionthe reaction mixture extracted with ether
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customto give an oil which
  8. extractionextracted with ether
  9. washThe extract was washed
  10. customdried
  11. customevaporated
  12. customto give a residue which

Sources & evidence

ORD record
ord-f84df7c2a41247d4afa11de5b3fdf51a
Source dataset
uspto-grants-1989_05
Patent number
US04833143

Reaction notes

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