4-Fluoroaniline → N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine

HRID 560537

反応式

HRID 560537 の反応式
FC1C=CC(N)=CC=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.[CH3:18][O:19][CH:20]([O:23][CH3:24])[CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][CH2:21][CH:20]([O:23][CH3:24])[O:19][CH3:18])=[CH:12][CH:11]=1

参加物

5

反応物 4

HCID 97314-FluoroanilineHCID 673264-FluorobenzylamineHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 11615438N-(2,2-dimethoxyethyl)-N-(4-fluorobenzyl)amine収率 71%

実験手順

Following the procedure as described in step A of Preparation 2, making variations as required to replace 4-fluoroaniline with 4-fluorobenzylamine to react with dimethoxyacetaldehyde followed by the imine reduction with sodium triacetoxyborohydride, N-(4-fluorobenzyl)-2,2-dimethoxyethanamine was obtained in 71% yield: 1H NMR (300 MHz, CDCl3) δ 7.24-7.19 (m, 2H), 6.97-6.89 (m, 2H), 4.43-4.39 (m, 1H), 3.70 (s, 2H), 3.30 (s, 6H), 2.67 (dd, J=5.4, 1.5 Hz, 2H); MS (ES+) m/z 214.3 (M+1).

後処理

  1. customas described in step A of Preparation 2

出典と根拠

ORDレコード
ord-a442cedb30bf4d6c8098e4c4b8036e5f
出典データセット
uspto-grants-2011_11
特許番号
US08063084B2

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