Hexylamine → N-Hexyl-3-methoxyaniline

HRID 412780

反応式

HRID 412780 の反応式
Cl[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:10]([NH2:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:10]([NH:16][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

参加物

6

反応物 3

HCID 8102HexylamineHCID 178333-ChloroanisoleHCID 23676156Sodium t-butoxide

生成物 1

HCID 15500485N-Hexyl-3-methoxyaniline収率 95.5%

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 1140Toluene溶媒

実験手順

3-Chloroanisole (74 mg, 0.52 mmol) reacted with n-hexylamine (65 mg, 0.64 mmol) according to procedure B using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and sodium tert-butoxide (58 mg, 0.60 mmol) in toluene at 100° C. to give the title compound (103 mg, 95%) as a colorless oil. Also 3-bromoanisole was converted to the title amine in 85% yield by procedure A: 1H-NMR (400 MHz, CDCl3): δ 6.99 (t, 1H, J=8.0 Hz), 6.19-6.13 (m, 2H), 6.08 (app.t, 1H, J=2.4 Hz), 3.70 (s, 3H), 3.55 (bs, 1H), 3.01 (t, 2H, J=7.2 Hz), 1.53 (m, 2H), 1.33 (m, 2H), 1.24 (m, 4H), 0.83 (t, 3H, J=6.8 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 160.81, 149.91, 129.87, 105.86, 102.09, 98.53, 55.01, 43.95, 31.61, 29.47, 26.81, 22.60, 14.01. GC/MS(EI): m/z 207 (M+), 136. Anal. Calcd for C13H21NO: C, 75.23; H, 10.21; N, 6.76. Found: C,75.25; H, 10.33; N, 6.86.

後処理

  1. customat 100° C.

出典と根拠

ORDレコード
ord-b8ec91d34adb4d23b0e16f478f980425
出典データセット
uspto-grants-2003_05
特許番号
US06562989B2

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