تفاعل #7183

معادلة التفاعل

5-benzoyl-2-chloromethylbenzimidazole

N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

N,N-diisopropylethylamine

→

product

المردود 75.9%

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

المردود 75.9%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was then cooled
2. 2
   تركيزconcentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL)
4. 4
   أخرىThe phases were separated
5. 5
   غسيلthe aqueous phase was washed with CH2Cl2 (2×25 mL)
6. 6
   غسيلThe combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL)
7. 7
   تجفيفdried (NaSO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated under reduced pressure
10. 10
    أخرىPurification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH)

الإجراء التجريبي

A solution of 5-benzoyl-2-chloromethylbenzimidazole (284 mg, 1.05 mmol), N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (476 mg, 1.04 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.08 mmol) were stirred at 80□ C in DMF (4 mL) for 16 hours. The reaction was then cooled, concentrated under reduced pressure and diluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL). The phases were separated and the aqueous phase was washed with CH2Cl2 (2×25 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL), dried (NaSO4), filtered and concentrated under reduced pressure. Purification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH) provided the desired alkylated product (468 mg, 65%) as an orange oil.

المصدر