Methane → HCID 86753053, compound

HRID 2392582Notes

Reaction equation

HRID 2392582 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]4[CH:28]=[C:27]5[C:22]([CH:23]=[CH:24][CH:25]=[CH:26]5)=[CH:21]4)[CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:29]=1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].C>C(O)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]4[CH:21]=[C:22]5[C:27]([CH:26]=[CH:25][CH:24]=[CH:23]5)=[CH:28]4)[CH2:14][CH2:15]3)=[CH:8][S:7][C:6]=2[CH:29]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 444266Maleic AcidHCID 18980211HCID 18980211, compound

Product 1

HCID 86753053HCID 86753053, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a 63° C. solution of 4-(6-fluorobenzo[b]thien-3-yl)-1-[4-(isoindol-2-yl)butyl]-piperazine (1.09 g, 2.66 mmol) in ethanol (40 mL) was added maleic acid (0.633 g, 5.45 mmol) and the resulting solution concentrated in vacuo to a dark foam. Trituration of the foam with ethanol/ethyl acetate gave a grey powder. The salt was treated with decolorizing charcoal in ethanol and recrystallized from ethanol to afford 1.08 g (63%) of the title compound as a grey powder, m.p. 153°-155° C.

Workup

  1. concentrationthe resulting solution concentrated in vacuo to a dark foam
  2. customTrituration of the foam with ethanol/ethyl acetate gave a grey powder
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6e36e2ab69d34427a7623c08b1ff14d2
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

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