Ammonia → HCID 19831295, compound

HRID 1493355Notes

Reaction equation

HRID 1493355 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH3:20])=[C:15]([CH3:19])[C:16]=1[O:17][CH3:18])=[O:11])[CH3:2].C([O-])(=O)/C=C/C([O-])=[O:25].[N+]([O-])([O-])=O.[Ce].[NH4+].N>S(=O)(=O)(O)O.ClCCl.CO>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH:20]=[O:25])=[C:15]([CH3:19])[C:16]=1[O:17][CH3:18])=[O:11])[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 5460307FumarateHCID 14647687HCID 14647687, compoundHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 19831295HCID 19831295, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (±) N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-methoxy-4,5-dimethylthiophene-2-carboxamide, fumarate (3 g) in dilute sulphuric acid (100 ml concentrated sulphuric acid in 500 ml water) was added ammonium cerium nitrate (17.56 g) in one portion. After stirring at room temperature for 0.5 hours and then cooling to 0° C., 0.88 ammonia solution (235 ml) was added dropwise to give a neutral solution. This was extracted several times with dichloromethane, the organic extracts combined and washed with water, dried over magnesium sulphate and the solvent removed in vacuo to give a light brown oil. Column chromatography on silica eluting with 10% methanol in dichloromethane gave the pure free base of the title compound, fumarate salt, m.p. 122°-123° C. (ex ethyl acetate-ethanol as recrystallising solvent).

Workup

  1. temperaturecooling to 0° C.
  2. customto give a neutral solution
  3. extractionThis was extracted several times with dichloromethane
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed in vacuo
  7. customto give a light brown oil
  8. customthe pure free base of the title compound, fumarate salt, m.p. 122°-123° C. (ex ethyl acetate-ethanol as recrystallising solvent)

Sources & evidence

ORD record
ord-52475cda3ed84ccf8f1541ff2731db10
Source dataset
uspto-grants-1991_06
Patent number
US05021449

Reaction notes

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