تفاعل #2180519

ord-5184306c7c584d0fb1aa938ec5c1adbd

معادلة التفاعل

Clc1ccnc2[nH]ccc12
4-chloro-1H-pyrrolo[2,3-b]pyridine
CNC1CCCN(Cc2ccccc2)C1
1-benzyl-N-methylpiperidin-3-amine
CN(c1ccnc2[nH]ccc12)C1CCCN(Cc2ccccc2)C1
orange oil
المردود 130.0%
CN(c1ccnc2[nH]ccc12)C1CCCN(Cc2ccccc2)C1
N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine
المردود 130.0%

ظروف التفاعل

درجة الحرارة
200°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL)
  2. 2
    غسيلthe organic phase was washed with sat. NaCl
  3. 3
    أخرىdried

الإجراء التجريبي

A sealed melted mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.18 g, 0.0012 mol) in 1-benzyl-N-methylpiperidin-3-amine (0.50 g, 0.0024 mol) was heated to 200° C. overnight. The reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL), and the organic phase was washed with sat. NaCl, then dried and was reduced under vacuum to give 500 mg of orange oil. The product was chromatographed with 7% MeOH/DCM, 0.7% NH4OH to give 192 mg of an orange oil (48.8% yield). 1H NMR (400 MHz, CDCl3): δ 7.98 (1H, d); 7.34 (5H, m); 7.08 (1H, d); 6.55 (1H, d); 6.2 (1H, d); 4.15 (1H, t); 3.47 (2H, q); 3.15 (1H); 3.1 (3H, s); 2.9 (11-1, d) 2.2-1.6 (6H, m). MS (M+H)+: 322.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08445488B2uspto-grants-2013_05