4-Methoxybenzylamine → 4,4'-(1-(4-fluorophenyl)pyrrolidine-2,5-diyl)bis(N-(4-methoxybenzyl)-2-nitroaniline)

HRID 2364787Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][C:16](Cl)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=3)[N:9]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:4][C:3]=1[N+:30]([O-:32])=[O:31].[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>ClCCl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([N:9]2[CH:10]([C:13]3[CH:18]=[CH:17][C:16]([NH:40][CH2:39][C:38]4[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=4)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=3)[CH2:11][CH2:12][CH:8]2[C:5]2[CH:6]=[CH:7][C:2]([NH:40][CH2:39][C:38]3[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=3)=[C:3]([N+:30]([O-:32])=[O:31])[CH:4]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 145 °C

Procedure

The product from Example 29A (0.88 g, 1.86 mmol) was combined with 4-methoxy benzylamine (3.64 mL, 28.0 mmol) and heated at 145° C. for 1 h in a microwave reactor. The mixture was diluted with dichloromethane and filtered. The filtrate was concentrated and purified by chromatography on silica gel with a 330 g column, eluting with 0-60% ethyl acetate/hexanes to give 0.79 g (62%) of an orange foam solid.

Workup

filtrationfiltered
concentrationThe filtrate was concentrated
custompurified by chromatography on silica gel with a 330 g column
washeluting with 0-60% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-fb9835022a08411b8ecda9ef8aa23dde
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691938B2

Reaction notes

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