4-Fluoroaniline → 2,2-dimethoxy-N-(4-(trifluoromethyl)benzyl)ethanamine

HRID 2067312Notes

Reaction equation

HRID 2067312 reaction equation
FC1C=CC(N)=CC=1.[F:9][C:10]([F:20])([F:19])[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.[CH3:21][O:22][CH:23]([O:26][CH3:27])[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:21][O:22][CH:23]([O:26][CH3:27])[CH2:24][NH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([C:10]([F:19])([F:20])[F:9])=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 97314-FluoroanilineHCID 768044-(Trifluoromethyl)benzylamineHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 606573432,2-dimethoxy-N-(4-(trifluoromethyl)benzyl)ethanamineYield 67%

Procedure

Following the procedure as described in step A of Preparation 2, making variations as required to replace 4-fluoroaniline with 4-(trifluoromethyl)benzylamine to react with dimethoxyacetaldehyde followed by the imine reduction with sodium triacetoxyborohydride, 2,2-dimethoxy-N-(4-(trifluoromethyl)benzyl)ethanamine was obtained in 67% yield: 1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=8.1 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 4.43 (t, J=2.7 Hz, 1H), 3.81 (s, 2H), 3.38 (s, 6H), 2.67 (dd, J=2.7, 2.5 Hz, 2H); MS (ES+) m/z 264.3 (M+1).

Workup

  1. customas described in step A of Preparation 2

Sources & evidence

ORD record
ord-2388ad98bb474ecc829a60b310ad5068
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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