Diisopropylethylamine → [3-(2-Benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amine

HRID 2219208Notes

Reaction equation

[CH2:1]([CH:10](N)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][C:5](OC)=CC=1.[CH2:21]([C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[O:35][CH2:36][CH2:37][CH2:38]Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([N:43](C(C)C)CC)(C)C.[C:49]([O-:52])(O)=O.[Na+]>O1CCOCC1.CCOC(C)=O>[CH2:21]([C:28]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=1[O:35][CH2:36][CH2:37][CH2:38][NH:43][CH:11]([C:10]1[CH:1]=[CH:2][C:7]([O:52][CH3:49])=[CH:6][CH:5]=1)[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 95 °C

Procedure

1,1-di(p-anisyl)methylamine (2.06 g, 8.48 mmol) is added to a stirred solution of 2-benzyl-1-(3-bromo-propoxy)-4-chloro-benzene (2.40 g, 7.07 mmol) and diisopropylethylamine (1.85 mL, 10.6 mmol) in anhydrous 1,4-dioxane (10 mL) at ambient temperature under nitrogen. The mixture is heated at 95° C. for 24 hours. At ambient temperature, EtOAc (100 mL) and half-saturated aqueous NaHCO3 solution (60 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 5-12% EtOAc in hexane) to give 3.08 g (6.13 mmol, 87% yield) of the title compound as oil. ESIMS: m/z 502 [(M+H)+, 35Cl], 504 [(M+H)+, 37Cl].

Workup

customThe organic layer is separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product is chromatographed on silica (gradient 5-12% EtOAc in hexane)

Sources & evidence

ORD record: ord-f65f54ef4a5f4b98a43f960618f5b499
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414063B2

Reaction notes

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