1-(2-Hydroxyethyl)piperazine → HCID 11965334, compound

HRID 2366368Notes

Reaction equation

HRID 2366368 reaction equation
N1(CCO)CCNCC1.BrC1SC(C=O)=CC=1.[OH:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[S:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:39][C:40]#[N:41]>>[CH3:34][O:35][C:36]1[CH:37]=[C:38](/[C:39](=[CH:32]/[C:30]2[S:31][C:27]([N:24]3[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][OH:18])[CH2:26][CH2:25]3)=[CH:28][CH:29]=2)/[C:40]#[N:41])[CH:42]=[CH:43][C:44]=1[O:45][CH3:46]

Participants

5

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 667273,4-DimethoxybenzeneacetonitrileHCID 784285-Bromothiophene-2-carbaldehydeHCID 64338745HCID 64338745, compound2×

Product 1

HCID 11965334HCID 11965334, compoundYield 49%

Procedure

Through the procedure as employed in Production step 1, an amine moiety derived from 1-piperazineethanol (7.81 g) was introduced into 5-bromothiophene-2-carboxaldehyde (3.82 g), to thereby yield 5-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-thiophene-2-carbaldehyde (yield: 3.22 g, 67%). The produced 5-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-thiophene-2-carbaldehyde (1.85 g) was condensed with 3,4-dimethoxybenzyl cyanide (1.37 g) through Method A (production step 2), to thereby yield the target product (yield: 1.51 g, 49%).

Sources & evidence

ORD record
ord-dbf7b385a5b64650b9100af56810d577
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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