Maleic Acid → HCID 10320318, compound

HRID 1196912Notes

Reaction equation

HRID 1196912 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH2:9]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[O:24])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCOCC>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH2:9]([N:16]1[CH2:17][CH2:18][CH:19]([CH2:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[O:24])[CH2:20][CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 9926747HCID 9926747, compound

Product 1

HCID 10320318HCID 10320318, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A saturated solution of maleic acid in ether (20 mL) was added to a solution of 1-benzyl-4-(2-(4''-fluorophenyl)-2'-oxoethyl)piperidine (186 mg, 0.59 mmol) in ether (10 mL) with stirring. The white precipitate was filtered and washed with copious amounts of ether. Drying in vacuo afforded a white powder (284 mg):mp 106°-108° C.; 1H-NMR:12.2-12.0(m,1H), 8.0(dd,2H,J=8,6), 7.5-7.35(m,5H), 7.15(t,2H,J=8), 6.4(s,2H), 4.2(s,2H), 3.65-3.4(m,2H), 2.95(d,2H,J=6), 2.9-2.7(m,2H), 2.4-1.6(m,4H); Anal.:Calcd for C20H22FNO.C4H4O4 0.25H2O:C,66.73, H,6.18, N,3.24; Found:C,66.50, H,5.97, N,3.10.

Workup

  1. filtrationThe white precipitate was filtered
  2. washwashed with copious amounts of ether
  3. customDrying in vacuo

Sources & evidence

ORD record
ord-e13530c4f15345b1a5e227f87140b68d
Source dataset
uspto-grants-1992_05
Patent number
US05116846

Reaction notes

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