4-Methyl-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1) → 4-Propyl-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1)
Reaction equation
[CH2:1]([C:4]1[CH:23]=[CH:22][C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[ClH:24].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[ClH:24].[CH2:1]([C:4]1[CH:23]=[CH:22][C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]Participants
3
Procedure
From 109g (6.0 g, 19.0 mmol), a similar procedure as described for 110a gave 110g (5.5 g, 82.5%) as yellow crystals, mp 118°-20° C. after recrystallization from ethyl acetate:methanol:hexane. 1H NMR (200 MHz, CDCl3) δ7.21 (d, J=8 Hz, 2H), 7.08 (d, J=8 Hz, 2H), 6.58 (s, 2H), 4.29 (s, 2H), 3.78 (s, 3H), 3.74 (s, 6H), 3.52 (t, J=8 Hz, 2H), 1.56 (sextet, J=8 Hz, 2H), 0.86 (t, J=8 Hz, 3H). Anal. (C19H26ClNO3) C, H, N.
Sources & evidence
- ORD record
- ord-579fb93286f243b3bdadea0eb8a9829c
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430062
Reaction notes
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