Dimethylamine → HCID 19599896, compound

HRID 611158Notes

Reaction equation

HRID 611158 reaction equation
[C:1]1(/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:14][CH2:13][C:12]3[O:15][CH:16]=[CH:17][C:11]=3[CH2:10]2)=[O:8])=[CH:3][CH:2]=1.[CH3:26][NH:27][CH3:28].[CH2:29]=O>C(O)(=O)C>[CH3:26][N:27]([CH2:29][C:16]1[O:15][C:12]2[CH2:13][CH2:14][N:9]([C:7]([C:4]3[CH:3]=[CH:2][C:1](/[CH:18]=[CH:19]/[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:6][CH:5]=3)=[O:8])[CH2:10][C:11]=2[CH:17]=1)[CH3:28]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 19600208HCID 19600208, compound

Product 1

HCID 19599896HCID 19599896, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.280 g (0.850 mmol) of (E)-5-(4-stilbenecarbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.115 ml (1.28 mmol) of 50% aqueous dimethylamine and 0.103 ml (1.28 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous solution of sodium hydrogen carbonate, and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform/methanol=50/1 to 25/1). The resulting product was washed with diethyl ether to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (chloroform/methanol=50/1 to 25/1)
  7. washThe resulting product was washed with diethyl ether

Sources & evidence

ORD record
ord-5394d78a5b0f40dc829347025a33da10
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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