3,4-Dimethoxybenzeneacetonitrile → HCID 11965580, compound

HRID 2366401Notes

Reaction equation

HRID 2366401 reaction equation
CN(C)CCNC.BrC1OC(C=O)=CC=1.[CH3:16][N: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]([CH2:21][CH2:22][N:17]([CH3:16])[CH3:18])[CH3:19])=[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 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 6003285-Bromofuran-2-carbaldehydeHCID 47384895-(4-Methyl-1-piperazinyl)-2-furancarboxaldehyde2×

Product 1

HCID 11965580HCID 11965580, compoundYield 96.9%

Procedure

Through the procedure as employed in Production step 1, an amine moiety derived from N,N,N′-trimethylethylenediamine (3.06 g) was introduced into 5-bromo-2-furaldehyde (1.75 g), to thereby yield 5-(4-methyl-piperazin-1-yl)-furan-2-carbaldehyde (yield: 1.18 g, 60%). The produced 5-(4-methyl-piperazin-1-yl)-furan-2-carbaldehyde (1.18 g) was condensed with 3,4-dimethoxybenzyl cyanide (1.06 g) through Method A (production step 2), to thereby yield the target product (yield: 2.06 g, 96%).

Sources & evidence

ORD record
ord-f7ded62eb2de4463b966541ace31a22a
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

Loading…