Hydrochloric Acid → HCID 15729913, compound

HRID 981994Notes

Reaction equation

HRID 981994 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH:26]1([Mg]Cl)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.CCOCC.Cl.C([O-])(O)=O.[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH:26]1([C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([OH:25])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:19]=[CH:20][C:21]([F:24])=[CH:22][N:23]=3)[CH2:14][CH2:13]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 1316951-(4-Fluorophenyl)-4-(4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl)butan-1-oneHCID 516892Sodium BicarbonateHCID 178478990HCID 178478990, compound

Product 1

HCID 15729913HCID 15729913, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A cold (15° C.) solution of 1-(4-fluorophenyl)-4-(4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl)-1-butanone (2.1 g, 6.1 mmol) in dry tetrahydrofuran (25 mL) kept under argon atmosphere was treated dropwise (15 min) with a solution of cyclohexylmagnesium chloride in ether (2.0M, 3.18 mL, 6.36 mmol). The cooling bath was removed and reaction mixture after being stirred at 23° C. for 2 h was treated dropwise (15 min) with HCl (2N, 3.5 mL), stirred for 15 min and diluted with CHCl3 (50 mL). The organic phase was basified with NaHCO3 and separated. Aqueous phase was extracted with CHCl3 (15 mL). The organic extracts were dried (MgSO4) and concentrated in vacuo to a sticky solid which was purified on silica gel column using a mixture of 40-100% AcOEt in CHCl3 as eluting solvent. The first group of fractions was concentrated in vacuo to give the carbinol as a solid, 1.1 g, 42%. The second group of fractions gave, after evaporation of solvent, the initial ketone 1.0 g, 48%. The carbinol was recrystallized from EtOH to give an analytical sample, mp 53°-9° C.

Workup

  1. customThe cooling bath was removed
  2. customreaction mixture
  3. stirringstirred for 15 min
  4. customseparated
  5. extractionAqueous phase was extracted with CHCl3 (15 mL)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo to a sticky solid which
  8. customwas purified on silica gel column
  9. additiona mixture of 40-100% AcOEt in CHCl3
  10. washas eluting solvent
  11. concentrationThe first group of fractions was concentrated in vacuo
  12. customto give the carbinol as a solid, 1.1 g, 42%
  13. customThe second group of fractions gave
  14. customafter evaporation of solvent
  15. customThe carbinol was recrystallized from EtOH
  16. customto give an analytical sample, mp 53°-9° C.

Sources & evidence

ORD record
ord-62170d232aae464ab184f526f045d035
Source dataset
uspto-grants-1991_02
Patent number
US04994460

Reaction notes

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