N-Methylbenzeneethanamine → 3,4-Dimethoxy-α-(1-methylethyl)-α-[3-[methyl(2-phenylethyl)amino]propyl]benzeneacetonitrile

HRID 587970Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][C:5]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)([CH:8]([CH3:10])[CH3:9])[C:6]#[N:7].[CH3:21][NH:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([C:5]([CH:8]([CH3:10])[CH3:9])([CH2:4][CH2:3][CH2:2][N:22]([CH3:21])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:6]#[N:7])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

Reactant 2

HCID 11503N-Methylbenzeneethanamine

HCID 135355715-Bromo-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile

Product 1

HCID 543026493,4-Dimethoxy-α-(1-methylethyl)-α-[3-[methyl(2-phenylethyl)amino]propyl]benzeneacetonitrile

Procedure

Reaction of 1f with N-methyl-2-phenylethanamine produced 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-(methyl(phenethyl)amino)pentanenitrile which was further reacted in a manner analogous to the procedure reported in Liang, C. D. et al., Tetrahedron Lett., (1986) 27, 1971-1974.

Sources & evidence

ORD record: ord-8de587a178774e51bb649100880e76f4
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227918B2

Reaction notes

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