반응 #49107

반응 방정식

dimethylamine dihydrochloride

Racemic {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine

Trisamine

2,6-dichlorobenzoic acid

1-hydroxybenzotriazole

dicyclohexylcarbodiimide

diisopropylethylamine

→

title product

수율 83.2%

(±)-2,6-Dichloro-N-[[1-(dimethylamino)cyclopentyl] (phenyl)methyl]benzamide

수율 83.2%

용매

DCM

N-methylpyrrolidinone

반응 조건

후처리

1. 1
   workup.ADDITIONwere then added
2. 2
   workup.STIRRINGshaking
3. 3
   workup.WAITcontinued overnight at room temperature
4. 4
   workup.STIRRINGafter shaking for a further 4 h
5. 5
   여과the mixture was filtered
6. 6
   세척the resins washed well with DCM and methanol
7. 7
   기타The filtrate was reduced in volume by evaporation in vacuo
8. 8
   세척Washing with DCM
9. 9
   세척methanol followed by elution with 1M ammonia in methanol

실험 절차

To a solution of 2,6-dichlorobenzoic acid (20 mg; 0.105 mmol) in DCM (2 ml) and N-methylpyrrolidinone (0.1-0.5 ml) was added 1-hydroxybenzotriazole (18 mg; 0.11 mmol) and PL-dicyclohexylcarbodiimide (88 mg; 0.14 mmol; Polymer Labs 1.59 mmol/g). The mixture was shaken at room temperature for 1 hour and then 1-[amino(phenyl)methyl]cyclopentyl}dimethylamine dihydrochloride D2 (20 mg; 0.07 mmol) and PS-diisopropylethylamine (82 mg; 0.21 mmol; Polymer Labs 2.59 mmol/g) were then added and shaking continued overnight at room temperature. An excess of PS-Trisamine was then added and after shaking for a further 4 h, the mixture was filtered and the resins washed well with DCM and methanol. The filtrate was reduced in volume by evaporation in vacuo and loaded onto an SCX cartridge (500 mg). Washing with DCM, then methanol followed by elution with 1M ammonia in methanol afforded the title product (22.8 mg). 1H NMR (CDCl3) δ: 0.98 (1H, m), 1.26 (1H, m), 1.40 (2H, m), 1.68 (2H, m), 1.85 (2H, m), 2.22 (6H, s), 5.08 (1H, bs), 7.27 (7H, m), and 7.47 (2H, m). Mass Spectrum (Electrospray LC/MS): Found 391 (MH+). C21H2435Cl2N2O requires 390. Ret. time 1.88 min.

출처