4-Methyl-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1) → 4-(Propan-2-yl)-N-[(3,4,5-trimethoxyphenyl)methyl]aniline--hydrogen chloride (1/1)
Reaction equation
[CH: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)([CH3:3])[CH3:2].[ClH:24].CC1C=CC(NCC2C=C(OC)C(OC)=C(OC)C=2)=CC=1>>[ClH:24].[CH: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)([CH3:3])[CH3:2]Participants
3
Procedure
From 109f (6.0 g, 18.9 mmol), a similar procedure as described for 110a gave 110f (4.4 g, 65.9%), as yellow crystals: mp 160°-2° C. after recrystallization from methanol:ethanol:water. 1H NMR (200 MHz, CDCl3) δ7.35 (d, J=8 Hz, 2H), 7.29 (d, J=8 Hz, 2H), 6.92 (s, 2H), 4.37 (s, 2H), 3.73 (s, 6H), 3.63 (s, 3H), 2.88 (h, J=6 Hz, 1H), 1.17 (d, J=6 Hz, 6H). Anal. (C19H26ClNO3) C, H, N.
Sources & evidence
- ORD record
- ord-cd7b000d7bbc445cb9f14c8c82942c14
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430062
Reaction notes
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