Methylamine → 2-[Methyl-(2-methyl-benzyl)-amino]-1-naphthalen-2-yl-ethanol
Reaction equation
C1(C)C(C=O)=CC=CC=1.[CH3:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].CN.[BH4-].[Na+].Br[CH2:25][C:26]([C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1)=[O:27]>>[CH3:10][N:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[CH2:25][CH:26]([C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1)[OH:27]Participants
6
Procedure
o-Tolualdehyde was converted to methyl-(2-methyl-benzyl)-amine via reductive amination using aqueous methyl amine and NaBH4. Methyl-(2-methyl-benzyl)-amine was then alkylated with 2-bromo-2′-acetonaphthone followed by reduction by NaBH4 to give 2-[methyl-(2-methyl-benzyl)-amino]-1-naphthalen-2-yl-ethanol as a clear, light yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.78-7.87 (m, 4H), 7.40-7.51 (m, 3H), 7.14-7.30 (m, 4H), 4.89 (dd, J=10.1, 3.9 Hz, 1H), 3.71 (d, J=12.9 Hz, 1H), 3.54 (d, J=12.9 Hz, 1H), 2.70 (dd, J=12.3, 10.3 Hz, 1H), 2.62 (dd, J=12.4, 3.9 Hz, 1H), 2.41 (s, 3H), 2.35 (s, 3H); Cl MS m/z 306 [C21H23NO+H]+.
Sources & evidence
- ORD record
- ord-ba223250b82644ffbf8f63f0056e540d
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236796B2
Reaction notes
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