2-Bromotoluene → Ethyl 1-benzylpiperidine-4-carboxylate

HRID 22282

Reaktionsgleichung

Reaktionsgleichung von HRID 22282
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C(N(CC)CC)C>C(Cl)Cl>[CH2:19]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:13]=1

Komponenten

5

Edukt 3

HCID 72362-BromotolueneHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Produkt 1

HCID 90423Ethyl 1-benzylpiperidine-4-carboxylateAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of ethyl isonipecotate (69.25 g, 0.441 mol). -bromotoluene (75.44 g, 52.4 ml, 0.441 mol) and triethylamine (44.74 g, 61.5 ml, 0.441 mol) in 1000 ml methylene chloride was stirred at r.t. for 20 hr. The mixture was washed with brine and the organic layer was separated, dried and concentrated to give 97.016 g of ethyl 1-benzylpiperidine-4-carboxylate as a yellow oil. HNMR (CDCl)δ 1.2(t, 3H), 1.6-1.9 (m, 4H), 2.0 (dt, 2H), 2.2-2.3 (m, 1H), 2.85 (m, 2H), 3.5 (s, 2H), 4.1 (q, 2H), 7.2-7.36 (m, 5H) ppm.

Aufarbeitung

  1. washThe mixture was washed with brine
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-81b691db5e8646d4bddd26ad65d6a6b9
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428043

Verknüpfte Notizen

Wird geladen…