1-(Pyridin-4-yl)ethan-1-amine → (6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-pyridin-4-yl-ethyl)-amine

HRID 2113120Notes

Reaction equation

HRID 2113120 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([CH2:17][NH:18][CH:19](C2C=NC=CC=2)[CH3:20])=[CH:5][CH:4]=1.[N:27]1[CH:32]=[CH:31][C:30](C(N)C)=[CH:29][CH:28]=1.COC1C(C2C=CC(OC)=CC=2)=CC(C=O)=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([CH2:17][NH:18][CH:19]([C:30]2[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=2)[CH3:20])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 2479981-(Pyridin-4-yl)ethan-1-amineHCID 5049666Sodium triacetoxyborohydrideHCID 223911916,4'-Dimethoxybiphenyl-3-carbaldehydeHCID 22391323(6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-pyridin-3-yl-ethyl)amine

Product 1

HCID 22391459(6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-pyridin-4-yl-ethyl)-amineYield 51%

Procedure

The title compound was prepared by the same procedure for preparing (6,4′-dimethoxy-biphenyl-3-ylmethyl)-(1-pyridin-3-yl-ethyl)-amine from 1-Pyridin-4-yl-ethylamine (245 mg, 2 mmol), 6,4′-Dimethoxy-biphenyl-3-carbaldehyde (121 mg, 0.5 mmol) and sodium triacetoxyborohydride (212 mg, 1.0 mmol, Aldrich). The title compound was purified by column chromatography (silica gel, ethyl acetate) in form as white solid in 51% yield (89 mg, 0.26 mmol).

Workup

  1. customThe title compound was purified by column chromatography (silica gel, ethyl acetate) in form as white solid in 51% yield (89 mg, 0.26 mmol)

Sources & evidence

ORD record
ord-76327541ca804d5b817224f6b2663cdd
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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