Water → 2-[(3-Furylmethyl)-(6-phenylhexyl)amino]ethanol

HRID 611077Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:2]1.Br[CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:21][CH2:22][OH:23])=[CH:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2.538 g (9.861 mmol) of N-(3-furylmethyl)-6-phenylhexylamine and 7.39 g (59.2 mmol) of 2-bromoethanol in 50 ml of N,N-dimethylformamide, 13.6 g (98.6 mmol) of potassium carbonate was added, followed by overnight stirring at 90° C. After cooling to room temperature, the reaction mixture was poured into water 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 (hexane/ethyl acetate=3/1 to 1/1) to yield the desired product.

Workup

temperatureAfter cooling to room temperature
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 (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record: ord-cbb2a820d27a474889577b73b0619c21
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998433

Reaction notes

Loading…