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

HRID 611186Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 0.230 g (0.748 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-2-(2-naphthoxy)ethan-1-one in 20 ml of acetic acid, 0.10 ml (1.1 mmol) of 50% aqueous dimethylamine and 0.092 ml (1.1 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 45 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide 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 (ethyl acetate/methanol=9/1 to 6/1) to yield the desired product.

Workup

distillationAfter the solvent was distilled off under reduced pressure
extractionextracted with dichloromethane 2 times
washThe combined organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=9/1 to 6/1)

Sources & evidence

ORD record: ord-57f0d85399504cd2afbb48674c85dcc6
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998433

Reaction notes

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