Benzylamine → 3-(4-{[6-(Benzylamino)hexyl]oxy}butyl)benzenesulfonamide

HRID 749234Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:23]([NH:30][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-[4-(6-Bromo-hexyloxy)-butyl]benzenesulfonamide (1.0 g) in toluene (4 ml) was added dropwise to benzylamine (0.65 g) and the resulting mixture heated at 80° C. for 6 h. The mixture was then cooled and 20% aqueous sodium hydroxide solution (50 ml) was added. The resulting mixture was extracted with ethyl acetate and the combined organic layers evaporated to dryness in vacuo. The residual oil was then purified by chromatography (DCM-IMS-NH3(aq) 100:10:1) to give the title compound (0.54 g) LC RT=3.89 min.

Workup

temperatureThe mixture was then cooled
extractionThe resulting mixture was extracted with ethyl acetate
customthe combined organic layers evaporated to dryness in vacuo
customThe residual oil was then purified by chromatography (DCM-IMS-NH3(aq) 100:10:1)

Sources & evidence

ORD record: ord-bd3f499aa4be4adf9a9b12a82dd0a673
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402598B2

Reaction notes

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