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

HRID 611103Notes

Reaction equation

[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([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)[CH2:5][C:4]=2[CH:3]=[CH:2]1.[CH3:28][NH:29][CH3:30].[CH2:31]=O>C(O)(=O)C>[CH3:28][N:29]([CH2:31][C:2]1[O:1][C:9]2[CH2:8][CH2:7][N:6]([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)[CH2:5][C:4]=2[CH:3]=1)[CH3:30]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 0.331 g (0.921 mmol) of 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-3-(3-phenethylphenyl) propan-1-one in 20 ml of acetic acid, 0.10 g (1.1 mmol) of 50% aqueous dimethylamine and 0.09 g (1.1 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 15 minutes. 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=4/1) to yield the desired product.

Workup

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

Sources & evidence

ORD record: ord-534b4944e5c846e886683878ec53ba52
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998433

Reaction notes

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