3,4-Dimethoxybenzeneacetonitrile → (Z)-2-(3,4-dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile

HRID 2366365Notes

Reaction equation

HRID 2366365 reaction equation
OC1CCNCC1.BrC1SC(C=O)=CC=1.[OH:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[S:27][C:26]([CH:28]=O)=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH2:35][C:36]#[N:37]>>[CH3:30][O:31][C:32]1[CH:33]=[C:34](/[C:35](=[CH:28]/[C:26]2[S:27][C:23]([N:20]3[CH2:19][CH2:18][CH:17]([OH:16])[CH2:22][CH2:21]3)=[CH:24][CH:25]=2)/[C:36]#[N:37])[CH:38]=[CH:39][C:40]=1[O:41][CH3:42]

Participants

5

Reactant 4

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 784285-Bromothiophene-2-carbaldehydeHCID 79341Piperidin-4-olHCID 27635405-(4-Hydroxypiperidin-1-yl)thiophene-2-carboxaldehyde2×

Product 1

HCID 16757522(Z)-2-(3,4-dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrileYield 50%

Procedure

Through the procedure as employed in Production step 1, an amine moiety derived from 4-hydroxypiperidine (3.03 g) was introduced into 5-bromothiophene-2-carboxaldehyde (1.91 g), to thereby yield 5-(4-hydroxypiperidin-1-yl)-thiophene-2-carbaldehyde (yield: 1.36 g, 64%). The produced 5-(4-hydroxypiperidin-1-yl)-thiophene-2-carbaldehyde (1.27 g) was condensed with 3,4-dimethoxybenzyl cyanide (1.06 g) through Method A (production step 2), to thereby yield the target product (yield: 1.09 g, 50%).

Sources & evidence

ORD record
ord-6b0602878a894ffeb920497da1f9d1c8
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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