تفاعل #1262119

معادلة التفاعل

rac-N2-methyl-N2-(1-methyl-piperidin-4-yl)-benzooxazole-2,5-diamine

pyridine

oxalyl chloride

4-butyl-benzoic acid

→

desired product

المردود 38.4%

4-Butyl-N-{2-[methyl-(1-methyl-piperidin-4-yl)-amino]-benzooxazol-5-yl}-benzamide

المردود 38.4%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   تركيزConcentrate the mixture in vacuo
2. 2
   workup.ADDITIONadd n-hexane
3. 3
   تركيزre-concentrate
4. 4
   workup.DISSOLUTIONre-dissolve in CH2Cl2
5. 5
   workup.ADDITIONAdd the resultant 4-butyl-benzoyl chloride solution
6. 6
   أخرىthe reaction mixture overnight
7. 7
   أخرىat room temperature
8. 8
   غسيلWash the mixture with saturated NaHCO3 (aq) (2×20 mL)
9. 9
   تجفيفdry the organic phase over Na2SO4
10. 10
    ترشيحfilter
11. 11
    تركيزconcentrate the mixture in vacuo
12. 12
    غسيلto silica gel flash column chromatography (3×4 g columns, eluting with 5% 2N NH3 in MeOH/CH2Cl2)

الإجراء التجريبي

Add oxalyl chloride (0.16 mL, 1.82 mmol) and 3 drops of DMF to a stirring suspension of 4-butyl-benzoic acid (0.162 g, 0.910 mmol) in CH2Cl2 (2.0 mL). Stir the reaction mixture at room temperature for 2 h. Concentrate the mixture in vacuo, add n-hexane, re-concentrate, and re-dissolve in CH2Cl2. Add the resultant 4-butyl-benzoyl chloride solution to a mixture of rac-N2-methyl-N2-(1-methyl-piperidin-4-yl)-benzooxazole-2,5-diamine (0.158 g, 0.607 mmol) and pyridine (0.05 mL) in CH2Cl2 (10 mL). Shake the reaction mixture overnight at room temperature. Wash the mixture with saturated NaHCO3 (aq) (2×20 mL), dry the organic phase over Na2SO4, filter, and concentrate the mixture in vacuo. Subject the residue to silica gel flash column chromatography (3×4 g columns, eluting with 5% 2N NH3 in MeOH/CH2Cl2) to yield the desired product as an oil (0.098 g, 35%). mass spectrum (m/e): 421.0 (M+1). 1H NMR (400 MHz, CDCl3): δ 7.84-7.78 (m, 1H), 7.78 (d, J=8.0 Hz, 2H), 7.48 (d, J=1.9 Hz, 1H), 7.35 (dd, J 8.8, 1.8 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.20 (d, J=8.8 Hz, 1H), 4.21-4.11 (m, 1H), 3.07 (s, 3H), 2.97 (d, J=11.2 Hz, 2H), 2.66 (t, J=8.0 Hz, 2H), 2.32 (s, 3H), 2.17 (t, J=11.6 Hz, 2H), 2.01-1.87 (m, 2H), 1.83-1.75 (m, 2H), 1.65-1.56 (m, 2H), 1.40-1.30 (m, 2H), 0.92 (t, J=7.2 Hz, 3H).

المصدر