Formaldehyde → 1-(2-diethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-3-(3-phenethylphenyl)propan-1-one

HRID 611183Notes

Reaction equation

HRID 611183 reaction equation
[O:1]1[C:5]2[CH2:6][N:7]([C:10](=[O:27])[CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:14]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29].[CH2:33]=O>C(O)(=O)C>[CH2:28]([N:30]([CH2:33][C:2]1[O:1][C:5]2[CH2:6][N:7]([C:10](=[O:27])[CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:14]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=1)[CH2:31][CH3:32])[CH3:29]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 196000361-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-3-(3-phenethylphenyl) propan-1-one

Product 1

HCID 196002351-(2-diethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-3-(3-phenethylphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.393 g (1.093 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-3-(3-phenethylphenyl) propan-1-one in 20 ml of acetic acid, 0.14 ml (1.3 mmol) of diethylamine and 0.11 g (1.3 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 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=9/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 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=9/1)

Sources & evidence

ORD record
ord-b7f151213b564654badf1eb21bba8b08
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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