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

HRID 1411423Notes

Reaction equation

HRID 1411423 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19](Cl)=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:26]2[CH:31]=[CH:30][C:29](Cl)=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH2:43])=[CH:40][CH:39]=1>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([NH:43][CH2:42][C:41]4[CH:44]=[CH:45][C:38]([O:37][CH3:36])=[CH:39][CH:40]=4)=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:26]2[CH:31]=[CH:30][C:29]([NH:43][CH2:42][C:41]3[CH:44]=[CH:45][C:38]([O:37][CH3:36])=[CH:39][CH:40]=3)=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 582268181-(4-Tert-butylphenyl)-2,5-bis(4-chloro-3-nitrophenyl)pyrrolidine

Product 1

HCID 866491004,4'-(1-(4-tert-butylphenyl)pyrrolidine-2,5-diyl)bis(N-(4-methoxybenzyl)-2-nitroaniline)Yield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-tert-Butylphenyl)-2,5-bis(4-chloro-3-nitrophenyl)pyrrolidine (4.41 g, 8.57 mmol) was combined, neat, with p-methoxy benzylamine (8.93 mL, 68.6 mmol) and heated at 145° C. for 1 hour. The mixture was diluted with dichloromethane and filtered. The filtrate was washed with 0.5 Al HCl, NaHCO3 solution, and then brine. The organic phase was concentrated and purified by chromatography on silica gel with an 80 g column, eluting with 0-50% ethyl acetate/hexanes to give 4.13 g (67%) of an orange foamy solid.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 0.5 Al HCl, NaHCO3 solution
  3. concentrationThe organic phase was concentrated
  4. custompurified by chromatography on silica gel with an 80 g column
  5. washeluting with 0-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0a0b94cc805b4e4593044989cd21d673
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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