Dimethylamine → HCID 67584930, compound

HRID 611419Notes

Reaction equation

HRID 611419 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[C:10]2[CH:15]=[CH:14][C:13]([S:16]([N:19]3[CH2:24][CH2:23][C:22]4[O:25][CH:26]=[CH:27][C:21]=4[CH2:20]3)(=[O:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:28][NH:29][CH3:30].[CH2:31]=O>C(O)(=O)C>[CH3:28][N:29]([CH2:31][C:26]1[O:25][C:22]2[CH2:23][CH2:24][N:19]([S:16]([C:13]3[CH:14]=[CH:15][C:10](/[CH:9]=[CH:8]\[C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)=[CH:11][CH:12]=3)(=[O:17])=[O:18])[CH2:20][C:21]=2[CH:27]=1)[CH3:30]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 67585497HCID 67585497, compound

Product 1

HCID 67584930HCID 67584930, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.693 g (1.733 mmol) of (Z)-5-(3-chlorostilbene-4'-sulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 10 ml of acetic acid, 0.23 g (2.60 mmol) of 50% aqueous dimethylamine and 0.21 g (2.60 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 0.5 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1); the resulting solid was washed with diethyl ether to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)
  6. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-a5483f7b157446739dc21279e4368201
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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