Oxalic Acid → HCID 19829420, compound

HRID 1493871Notes

Reaction equation

HRID 1493871 reaction equation
Br[CH2:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.Cl.[C:15]1([N:21]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(O)(=O)C(O)=O>CC(=O)CC.CC(C)=O>[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:4]([CH2:3][CH2:2][N:34]2[CH2:35][CH2:36][CH:31]([N:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:32][CH2:33]2)[CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 143302824-(2-bromoethyl)-3,4-dihydro-2H-benzopyranHCID 19829422HCID 19829422, compound

Product 1

HCID 19829420HCID 19829420, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure is as in Example 4, but starting with 4-(2-bromoethyl)-3,4-dihydro-2H-benzopyran (1.6 g), N-phenyl-N(4-piperidyl)-4-fluorobenzamide hydrochloride (2.21 g), dry potassium carbonate (1.8 g) and potassium iodide (0.8 g) in 2-butanone (50 cc). The oil obtained is taken up in the minimum amount of acetone and oxalic acid (0.6 g), dissolved in acetone, is added. The white precipitate formed is filtered off on sintered glass and then recrystallized in ethanol (50 cc). N-{1-[2-(3,4-Dihydro-2H-1-benzopyran-4-yl)ethyl]-4-piperidyl}-N-phenyl-4-fluorobenzamide acid oxalate (2.7 g) is thereby obtained in the form of a white solid, m.p. 161° C.

Workup

  1. customThe oil obtained
  2. additionis added
  3. customThe white precipitate formed
  4. filtrationis filtered off on sintered glass
  5. customrecrystallized in ethanol (50 cc)

Sources & evidence

ORD record
ord-341b4691aa6f4a6f9291a795cdb1bba8
Source dataset
uspto-grants-1991_06
Patent number
US05025013

Reaction notes

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