3,4-Dimethoxybenzeneacetonitrile → HCID 11965419, compound

HRID 2366381Notes

Reaction equation

HRID 2366381 reaction equation
OC1CCNCC1.BrC1OC(C=O)=CC=1.[OH:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[O: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[O: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 79341Piperidin-4-olHCID 6003285-Bromofuran-2-carbaldehydeHCID 62126294HCID 62126294, compound2×

Product 1

HCID 11965419HCID 11965419, compoundYield 65%

Procedure

Through the procedure as employed in Production step 1, an amine moiety derived from 4-hydroxypiperidine (1.52 g) was introduced into 5-bromo-2-furaldehyde (875 mg), to thereby yield 5-(4-hydroxy-piperidin-1-yl)-furan-2-carbaldehyde (yield: 660 mg, 68%). The produced 5-(4-hydroxy-piperidin-1-yl)-furan-2-carbaldehyde (390 mg) was condensed with 3,4-dimethoxybenzyl cyanide (354 mg) through Method A (production step 2), to thereby yield the target product (yield: 458 mg, 65%).

Sources & evidence

ORD record
ord-4716d0bebd7548a2ab6dc6633cf9faa6
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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