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

HRID 22282

Reaction equation

HRID 22282 reaction equation
[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

Participants

5

Reactant 3

HCID 72362-BromotolueneHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 90423Ethyl 1-benzylpiperidine-4-carboxylateYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-81b691db5e8646d4bddd26ad65d6a6b9
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Linked notes

Loading…