Hydrochloric Acid → HCID 70083155, compound

HRID 1614631Notes

Reaction equation

HRID 1614631 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Cl.Cl[CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.[C:36](=[O:39])([OH:38])[O-:37].[Na+].Cl.C[OH:43].C([O:46][CH2:47]C)C>C(O)C.C(Cl)(Cl)Cl.C(Cl)Cl>[OH2:37].[C:47]([OH:46])(=[O:43])[C:36]([OH:38])=[O:39].[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 19771957N,alpha-bis(4-fluorophenyl)-4-piperidinemethanamineHCID 21864698Diethyl ether methanol

Product 1

HCID 70083155HCID 70083155, compoundYield 17.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N,α-bis(4-fluorophenyl)-4-piperidinemethanamine (4.23 g, 0.014 mol), 2-(chloromethyl)quinoline monohydrochloride (3.00 g, 0.014 mol), and sodium bicarbonate (2.42 g, 0.029 mol) was stirred 32 h at room temperature in 350 mL of ethanol (200). The reaction was concentrated to dryness, and the residue obtained was dissolved in chloroform. The chloroform layer was extracted with water. The chloroform layer was dried (Na2SO4) and filtered. When the chloroform was removed by rotary evaporator, a dark brown oil was obtained. This oil was dissolved in methylene chloride and subjected to flash chromatography on silica gel. Elution was accomplished using methylene chloride, 1% methanol-methylene chloride, and 2% methanol-methylene chloride. Fractions of similar purity were combined, and the solvents were removed to give a brown oil. Attempts to prepare a crystalline HCl salt gave a substance which was extremely hydroscopic. This material was converted to the free base and subjected again to flash chromatography using the same solvent systems for elution. A brown oil was obtained and converted to the oxalate salt in methanol-diethyl ether. A white solid was isolated and dried in vacuo 16 h at 100° C. This process furnished 1.36 g (17.9%) of white crystalline solid, mp 180°-182° C.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customthe residue obtained
  3. extractionThe chloroform layer was extracted with water
  4. dry with materialThe chloroform layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customWhen the chloroform was removed by rotary evaporator
  7. customa dark brown oil was obtained
  8. washElution
  9. customthe solvents were removed
  10. customto give a brown oil
  11. customgave a substance which
  12. washfor elution
  13. customA brown oil was obtained
  14. customA white solid was isolated
  15. customdried in vacuo 16 h at 100° C

Sources & evidence

ORD record
ord-feaa7c017fe44ebd9190d7abb015c386
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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