Acetonitrile → HCID 14739894, compound

HRID 1164975Notes

Reaction equation

HRID 1164975 reaction equation
C1(C[CH:8]2[CH2:13][NH:12][CH2:11][CH2:10][N:9]2[C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)C=CC=CC=1.[CH3:21][S:22]([O:25]S(C)(=O)=O)(=O)=[O:23].[C:30](#N)[CH3:31]>>[C:30]1([CH2:31][N:12]2[CH2:13][CH2:8][N:9]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][S:22]([CH3:21])(=[O:25])=[O:23])=[CH:18][CH:19]=3)[CH2:10][CH2:11]2)[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 6342Acetonitrile2×HCID 81560Methanesulfonic anhydrideHCID 21798565HCID 21798565, compound

Product 1

HCID 14739894HCID 14739894, compound

Procedure

To a chilled solution of 9150 g (35.5 mmol) of 4-[4-(phenylmethyl-1-piperazinyl]benzenamine in 100 mL of acetonitrile, add 6.49 g (37 mmol) of methanesulfonic anhydride in 50 mL of acetonitrile. Allow the reation mixture to stir at room temperature for 5 h. After this time, filter the resulting precipitate, add 100 mL of saturated aqueous sodium bicarbonate solution and extract this solution with 2×100 mL of methylene chloride. Wash the combined methylene chloride layers with 100 mL of saturated aqueous sodium chloride solution. Remove the solvent in vacuo. Dissolve the residue in 100 mL of methanol and acidify the solution with hydrogen chloride gas to pH=1. The solution is cooled and the resulting solid filtered to obtain the title compound.

Workup

  1. filtrationAfter this time, filter the resulting precipitate
  2. additionadd 100 mL of saturated aqueous sodium bicarbonate solution
  3. extractionextract this solution with 2×100 mL of methylene chloride
  4. washWash the combined methylene chloride layers with 100 mL of saturated aqueous sodium chloride solution
  5. customRemove the solvent in vacuo
  6. dissolutionDissolve the residue in 100 mL of methanol
  7. temperatureThe solution is cooled
  8. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-ebe44c00faa24b64b6b6b151b71bc9f3
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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