4-Methyl-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1) → 4-Ethyl-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1)
Reaction equation
[CH2:1]([C:3]1[CH:22]=[CH:21][C:6]([NH:7][CH2:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[ClH:23].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[ClH:23].[CH2:1]([C:3]1[CH:22]=[CH:21][C:6]([NH:7][CH2:8][C:9]2[CH:10]=[C:11]([O:19][CH3:20])[C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=2)=[CH:5][CH:4]=1)[CH3:2]Participants
3
Procedure
From 109b (4.0 g, 13.2 mmol), a similar procedure as described in 110a gave 110b (3.17 g, 70.7%), as yellow crystals: mp 155°-7° C. after recrystallization from ethanol and methanol. 1H NMR (200 MHz, CDCl3) δ7.20 (s, br, 4H), 6.86 (s, 2H), 4.34 (s, 2H), 3.72 (s, 6H), 3.62 (s, 3H), 2.55 (q, J=8 Hz, 2H), 1.13 (t, J=8 Hz, 3H). Anal. (C18H24ClNO3).
Sources & evidence
- ORD record
- ord-a1c5624a22b047f3a68876df83236930
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430062
Reaction notes
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