Oxalic Acid → HCID 70083728, compound

HRID 1614639Notes

Reaction equation

HRID 1614639 reaction equation
O.Cl.[F:3][C:4]1[CH:5]=[C:6]([NH:11][CH:12]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[F:10].Cl[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1.C(=O)([O-])[O-:39].[Na+].[Na+].[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46]>C(O)C.CO.CCOCC>[OH2:39].[C:44]([OH:49])(=[O:48])[C:45]([OH:47])=[O:46].[F:3][C:4]1[CH:5]=[C:6]([NH:11][CH:12]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH:13]2[CH2:18][CH2:17][N:16]([CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

8

Reactant 4

HCID 971Oxalic AcidHCID 10340Sodium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 19772069HCID 19772069, compound

Product 1

HCID 70083728HCID 70083728, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.60 g (8.8 mmol) of 4-[[(3,4-difluorophenyl)amino](4-fluorophenyl)methyl]piperidine hydrochloride hydrate, 2.04 g (9.5 mmol) of 2-chloromethylquinoline and 3.0 g (28.3 mmol) of sodium carbonate in 200 mL of absolute ethanol was stirred at room temperature for 66 h. The solvent was removed in vacuo to give an oil. This was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (Na2SO4), and the solvent was removed in vacuo to give an oil. A solution of the oil in methanol was treated with an excess of oxalic acid. Anhydrous ether was added, and 2.53 g (51.3%) of title compound was collected as a crystalline solid, mp. 139°-140° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give an oil
  3. customThis was partitioned between CH2Cl2 and dilute NaOH
  4. dry with materialThe CH2Cl2 solution was dried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. custom2.53 g (51.3%) of title compound was collected as a crystalline solid, mp. 139°-140° C.

Sources & evidence

ORD record
ord-e19bc1f066bf4a1faad17c6a63eba2c7
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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