4-Methoxybenzylamine → N-(4-methoxybenzyl)(8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine

HRID 216763Notes

Reaction equation

HRID 216763 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[C:8]([CH:22]=O)=[CH:7]2.[CH2:24]([NH2:33])[C:25]1[CH:32]=[CH:31][C:28]([O:29][CH3:30])=[CH:27][CH:26]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH3:30][O:29][C:28]1[CH:31]=[CH:32][C:25]([CH2:24][NH:33][CH2:22][C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]([F:21])([F:20])[F:19])=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 575561608-Methyl-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde

Product 1

HCID 57707763N-(4-methoxybenzyl)(8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Prepared according to Procedure F using 8-methyl-2-(2-(trifluoromethyl)phenyl)-quinoline-3-carbaldehyde (1 g, 3.17 mmol), DCE (16 mL), PMBNH2 (0.62 mL, 4.75 mmol, 1.5 eq), and NaBH(OAc)3 (2.0166 g, 9.52 mmol, 3 eq). After purification, N-(4-methoxybenzyl)(8-methyl-2-(2-(trifluoromethyl)phenyl)-quinolin-3-yl)methanamine was obtained as light yellow syrup. 1H NMR (DMSO-d) δ ppm 8.48 (1H, s), 7.87 (2H, t, J=7.2 Hz), 7.64-7.77 (2H, m), 7.48-7.62 (3H, m), 7.14 (2H, d, J=8.6 Hz), 6.81 (2H, d, J=8.6 Hz), 3.71 (3H, s), 3.44-3.62 (4H, m), 2.61 (3H, s), 2.54 (1H, s). Mass Spectrum (ESI) m/e=437.2 (M+1).

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-b0f30dcc3d19474b931171dfeabcddee
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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