Morpholine → 3-acetyl-7-(morpholin-4-yl)sulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 33215Notes

Reaction equation

[C:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([S:15](Cl)(=[O:17])=[O:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N(CC)CC)C>O1CCCC1>[C:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([S:15]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)(=[O:17])=[O:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-acetyl-7-chlorosulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine (4.0 g, 13.9 mmol), morpholine (1.8 ml, 20.8 mmol) and triethylamine (2.14 ml, 15.3 mmol) in tetrahydrofuran (120 ml) was heated at 60° C. for 3 h. The reaction mixture was then cooled, filtered and the filtrate evaporated in vacuo to give a yellow solid. Crystallisation from dichloromethane/n-hexane gave the title compound as an off-white solid (4.4 g, 94 Mass Spectrum AP+: Found 339 (MH+). C16H22N2SO4 requires 338.

Workup

temperatureThe reaction mixture was then cooled
filtrationfiltered
customthe filtrate evaporated in vacuo
customto give a yellow solid
customCrystallisation from dichloromethane/n-hexane

Sources & evidence

ORD record: ord-eba04d1872994fd2ad08fbbcd83660ef
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429579B2

Reaction notes

Loading…