Formaldehyde → HCID 131724984, compound

HRID 1070765Notes

Reaction equation

HRID 1070765 reaction equation
[C:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])#[C:2][CH3:3].[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.[CH2:36]=O>O1CCOCC1.S([O-])([O-])(=O)=O.[Cu+2]>[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[N:30]2[CH2:31][CH2:32][N:33]([CH2:36][C:3]#[C:2][CH2:1][N:4]3[C:12](=[O:13])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]3=[O:14])[CH2:34][CH2:35]2)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 23284207HCID 23284207, compound

Product 1

HCID 131724984HCID 131724984, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 312751,4-DioxaneSolvent

Procedure

15 g (81 mmol) 2-propinyl-isoindolin-1,3-dione, 15 g (52 mmol) [bis-(4-fluorophenyl)-methyl]-piperazine, 2:5 g (81 mmol) paraformaldehyde and 0,2 g copper sulfate are stirred for three hours in 200 ml dioxane at 100° C. The cool solution is concentrated under vacuum and the residue is distributed between acetic acid ethyl ester and saturated NaCl solution. The organic phase is dried over sodium sulfate and concentrated under vacuum until dry. The residue is chromatographically purified over silica gel with acetic acid ethyl ester/petroleum ether (1/1): Yield 23.4 g (93%) yellow amorphous solid.

Workup

  1. concentrationThe cool solution is concentrated under vacuum
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customuntil dry
  5. customThe residue is chromatographically purified over silica gel with acetic acid ethyl ester/petroleum ether (1/1)

Sources & evidence

ORD record
ord-5307b8964f0545f5b063244089258f9c
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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