Sodium cyanoborohydride → (6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-quinolin-8-yl-ethyl)-amine

HRID 1072245

Reaction equation

HRID 1072245 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](C2C3C(=CC=CC=3)N=CC=2)[CH3:20])=[CH:5][CH:4]=1.[N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][C:39]=2C(N)C)[CH:34]=[CH:33][CH:32]=1.COC1C(C2C=CC(OC)=CC=2)=CC(C=O)=CC=1.C([BH3-])#N.[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:39]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:40]=2[N:31]=[CH:32][CH:33]=[CH:34]3)[CH3:20])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 122087931-(Quinolin-8-yl)ethan-1-amineHCID 223911916,4'-Dimethoxybiphenyl-3-carbaldehydeHCID 22391337(6,4'-Dimethoxybiphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine

Product 1

HCID 22391354(6,4'-Dimethoxy-biphenyl-3-ylmethyl)-(1-quinolin-8-yl-ethyl)-amineYield 72%

Procedure

The title compound was prepared by the same procedure for (6,4′-dimethoxy-biphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine from 1-quinolin-8-yl-ethylamine (510 mg, 3.0 mmol), 6,4′-Dimethoxy-biphenyl-3-carbaldehyde (242 mg, 1.0 mmol) and sodium cyanoborohydride (1.0 g, 16 mmol, Aldrich). The title compound was purified by column chromatography (silica gel, ethyl acetate) in form as white solid in 72% yield (287 mg, 0.72 mmol).

Workup

  1. customThe title compound was purified by column chromatography (silica gel, ethyl acetate) in form as white solid in 72% yield (287 mg, 0.72 mmol)

Sources & evidence

ORD record
ord-8e9cc16328864b5b961fcf372cd99578
Source dataset
uspto-grants-2005_06
Patent number
US06908935B2

Linked notes

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