반응 #673395

반응 방정식

oxalyl chloride

4-(4-pyridyl)benzoic acid

oxalyl chloride

2-(hydroxymethyl)-4-(6-bromonaphth-2-ylsulphonyl)piperazine

triethylamine

→

1-(6-bromonaphth-2-ylsulphonyl)-3-(hydroxymethyl)-4-[4-(4-pyridyl)benzoyl] piperazine

수율 56.6%

용매

DMF

dichloromethane

DMF

dichloromethane

water

반응 조건

후처리

1. 1
   workup.STIRRINGthe suspension stirred a further 4 hours
2. 2
   기타The solvent was removed in vacuo
3. 3
   기타the residue, after drying
4. 4
   workup.STIRRINGAfter stirring at room temperature overnight the reaction mixture
5. 5
   여과was filtered off
6. 6
   기타dried
7. 7
   기타recrystallised from ethyl acetate (10 ml)

실험 절차

A stirred suspension of 4-(4-pyridyl)benzoic acid (sodium salt) (190 mg, 0.86 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.2 ml, 2.3 mmol) and DMF (catalytic amount). After stirring for 2 hours, further oxalyl chloride 0.2 ml, 2.3 mmol) and DMF (catalytic amount) was added and the suspension stirred a further 4 hours. The solvent was removed in vacuo and the residue, after drying, was suspended in dichloromethane (20 ml) and treated with 2-(hydroxymethyl)-4-(6-bromonaphth-2-ylsulphonyl)piperazine (300 mg, 0.78 mmol) and triethylamine (0.36 ml, 2.5 mmol). After stirring at room temperature overnight the reaction mixture was diluted with dichloromethane (20 ml) and water (20 ml). A copious precipitate appeared which was filtered off, dried and recrystallised from ethyl acetate (10 ml) to yield 1-(6-bromonaphth-2-ylsulphonyl)-3-(hydroxymethyl)-4-[4-(4-pyridyl)benzoyl] piperazine as a colourless solid (250 mg); 1H NMR (300 MHz, DMSO-d6) δ=3-4 ppm (broad, 9H), δ7.2 ppm (d, 2H), δ=7.7 ppm (d, 2H), δ=7.8 ppm (m, 4H), δ=8.2 ppm (t, 2H), δ8.4 ppm (s,1H), δ=8.45 ppm (s,1H), δ=8.6 ppm (d, 2H); signals due ethyl acetate (1 mol eq) were also present; MS: (M+H)+ 566/568 (1 Br pattern); analysis; found: C, 56.8; H, 4.9; N, 6.3%; C27H24BrN3SO4. C4H8O2 requires: C, 56.9; H, 4.9; H, 4.9; N, 6.4%.

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