Acetonitrile → n-[4-[(3-Hydroxyphenyl)piperazine-1-yl]butyl]-3,4-dihydronaphtalene-2-carboxamide

Reaktionsgleichung

Br[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([CH:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:8].[OH:19][C:20]1[CH:21]=[C:22](N2CCNCC2)[CH:23]=[CH:24][CH:25]=1.C([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])C.CC#[N:41]>>[OH:19][C:20]1[CH:21]=[C:22]([CH:35]2[CH2:36][NH:41][CH2:38][CH2:37][N:34]2[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)=[O:8])[CH:23]=[CH:24][CH:25]=1

Komponenten

Edukt 4

HCID 6342Acetonitrile

HCID 8471Triethylamine

HCID 27365971-(3-Hydroxyphenyl)piperazine

HCID 66852491n-(4-Bromobutyl)-dihydro-2-naphtylcarboxamide

Produkt 1

HCID 23135106n-[4-[(3-Hydroxyphenyl)piperazine-1-yl]butyl]-3,4-dihydronaphtalene-2-carboxamideAusbeute 54 %

Versuchsvorschrift

A mixture of the bromo adduct E1 (100 mg, 0.32 mmol), of commercial 3-hydroxyphenyl piperazine (57 mg, 0.32 mmol) and triethylamine (0.07 mL, 0.5 mmol) in CH3CN are reluxed during 16 h. The solvent is evaporated and the residue is taken up in CH2Cl2 (15 mL), washed with brine, dried and concentrated. The residue is purified by chromatography eluting with AcOEt:MeOH (9/1) to yield the titled adduct (mp 152° C., 70 mg, 54%)