Dimethylamine → HCID 19599879, compound

HRID 611407Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 0.210 g (0.572 mmol) of 5-(4-benzoylphenylsulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 10 ml of acetic acid, 77 mg (0.86 mmol) of 50% aqueous dimethylamine and 70 mg (0.86 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 0.5 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with ethyl acetate 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 crystallized from diethyl ether-hexane to yield the desired product.

Workup

distillationAfter the solvent was distilled off under reduced pressure
extractionextracted with ethyl acetate 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 crystallized from diethyl ether-hexane

Sources & evidence

ORD record: ord-cb340fe02a724c5fb90ff84a8f444966
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998433

Reaction notes

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