تفاعل #9033

معادلة التفاعل

Allyl bromide

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

N,N-diisopropylethylamine

→

foam

المردود 56.6%

1H-benzimidazol-2-ylmethyl -(4-diallylaminomethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

المردود 56.6%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed consecutively with H2O (2×5 mL), saturated aqueous NaHCO3 (5 mL) and saturated aqueous NaCl (5 mL)
2. 2
   استخلاصThe aqueous layer was extracted with CH2Cl2 (20 mL)
3. 3
   تجفيفthe combined organic extracts were dried (MgSO4)
4. 4
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

To a solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (156 mg, 0.39 mmol) in CH2Cl2 (4 mL) was added N,N-diisopropylethylamine (65 μL, 0.37 mmol). Allyl bromide (35 μL, 0.40 mmol) was added dropwise and the resultant mixture stirred at room temperature for 3 days. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed consecutively with H2O (2×5 mL), saturated aqueous NaHCO3 (5 mL) and saturated aqueous NaCl (5 mL). The aqueous layer was extracted with CH2Cl2 (20 mL) and the combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to afford a light yellow foam (100 mg). Purification by column chromatography on silica gel (200:1:1 followed by 100:1:1—CH2Cl2:MeOH:NH4OH) followed by radial chromatography on silica gel (1000:1:1—EtOAc:MeOH:NH4OH) afforded AMD9725 (24.5 mg, 14%) as a light yellow foam. 1H NMR (CDCl3) δ 1.62–1.75 (m, 1H), 1.97–2.08 (m, 2H), 2.22–2.30 (m, 1H), 2.66–2.77 (m, 1H), 2.77–2.92 (m, 1H), 3.01 (d, 4H, J=6.3 Hz), 3.48 (s, 2H), 3.74 (s, 2H), 3.99 (d, 1H, J=16.8 Hz), 4.07–4.12 (m, 1H), 4.18 (d, 1H, J=16.8 Hz), 5.09–5.17 (m, 4H), 5.83 (ddt, 2H, J=16.8, 10.2, 6.3 Hz), 7.15–7.20 (m, 5H), 7.34 (d, 2H, J=7.8 Hz), 7.41 (d, 1H, J=7.8 Hz), 7.48–7.56 (m, 1H), 7.60–7.69 (m, 1H), 8.69 (d, 1H, J=4.2 Hz); 13C NMR (CDCl3) δ 19.69, 21.65, 27.53, 46.90, 52.08, 54.63, 55.44, 58.47, 109.24, 115.61, 117.04, 119.79, 120.49, 126.67, 127.13, 132.99, 134.17, 135.45, 136.13, 136.56, 145.22, 154.64, 155.80. ES-MS m/z 478.4 (M+H). Anal. Calcd. for C31H35N5.0.5H2O: C, 76.51; H, 7.46; N, 14.39. Found: C, 76.67; H, 7.45; N, 14.18.

المصدر