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

HRID 611129Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 0.120 g (0.396 mmol) of 5-(4-phenylbenzoyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.054 ml (0.59 mmol) of 50% aqueous dimethylamine and 0.048 ml (0.59 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 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 sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1 to 25/1) 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 (chloroform to chloroform/methanol=50/1 to 25/1)

Sources & evidence

ORD record: ord-904e889d24154eeca76a22a51a399b11
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998433

Reaction notes

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