1-benzyl-N-methylpiperidin-4-amine → U 99363

HRID 1417857

Reaction equation

HRID 1417857 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][CH:20]=[CH:19][N:18]=1>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:15])[C:17]2[C:22]([O:23][CH2:24][CH3:25])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 106319262-BROMO-3-ETHOXYPYRIDINE

Product 1

HCID 133107U 99363

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(1-benzylpiperidin-4-yl)-N-methylamine (XXVII, 4.80 g) and 2-bromo-3-ethoxypyridine (XXVIIIa, 2.3805 g) is placed in a metal, screw cap reaction vessel using dichloromethane as the transfer solvent. Reduced pressure is applied to the vessel with heating at 50° to 60° for 45 min to remove dichloromethane. The vessel is then sealed and heated at 160° to 165° for 2 days. After cooling, the resulting solids are dissolved in dichloromethane and washed with water and saline. The organic phases are dried over magnesium sulfate and concentrated under reduced pressure to give the product, which is chromatographed (silica gel; eluting with ethyl acetate/hexane (30/70) followed by ethyl acetate/hexane (50/50)), to give N-(1-benzylpiperidin-4-yl)-N-(3-ethoxypyridin-2-yl)-methylamine (XXVIII, Chart G); MS (m/z) 325; IR (neat) 1462, 1211, 1481, 1589 and 1450 cm-1.

Workup

  1. customcap
  2. customreaction vessel
  3. temperaturewith heating at 50° to 60° for 45 min
  4. customto remove dichloromethane
  5. customThe vessel is then sealed
  6. temperatureheated at 160° to 165° for 2 days
  7. temperatureAfter cooling
  8. dissolutionthe resulting solids are dissolved in dichloromethane
  9. washwashed with water and saline
  10. dry with materialThe organic phases are dried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customto give the product, which
  13. customis chromatographed
  14. wash(silica gel; eluting with ethyl acetate/hexane (30/70) followed by ethyl acetate/hexane (50/50))

Sources & evidence

ORD record
ord-cc319317b3864991820ceff95256e646
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Linked notes

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