Water → {2-[4-(2-Azepan-1-ylethoxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamine

HRID 1950333Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=3)[CH2:21]2)=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:39][CH2:40][N:41]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.O>CN(C)C=O>[N:41]1([CH2:40][CH2:39][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][NH:10][CH2:9][C:7]3[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[CH:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=4)[CH2:21]3)=[CH:14][CH:15]=2)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-{2-{[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]methylamino}ethyl}phenol (160 mg) in N,N-dimethylformamide (3 ml) were sequentially added potassium carbonate (100 mg) and 1-(2-chloroethyl)azepane (110 mg), and the solution was stirred for 2 hours at 60° C. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (157 mg).

Workup

stirringby stirring
extractionthe solution was extracted with ethyl acetate
washsequentially washed with water and brine
customthe solvent was evaporated in vacuo
customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record: ord-15e13cc1a6364623a1ff1181199823af
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399520B2

Reaction notes

Loading…