Dimethylamine → N,N-dimethyl-[6-[4-(2-methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

HRID 611271Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 0.250 g (0.724 mmol) of 6-[4-(2-methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.098 ml (1.09 mmol) of 50% aqueous dimethylamine and 0.088 ml (1.09 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 120 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with dichloromethane 2 times. The combined organic layer was washed with water and 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/methanol=5/1) 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 magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)

Sources & evidence

ORD record: ord-17cf343580ad4c549c03b301eadace28
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998433

Reaction notes

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