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

HRID 361812

Reaction equation

HRID 361812 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>C(Cl)Cl>[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 1-benzyl-4-(methylamino)piperidine (EXAMPLE 9, 2.92 g) and 2-bromo-3-ethoxypyridine (EXAMPLE 69, 1.44 g) is stirred at 160°-165° in a sealed tube for 2 days, diluted with methylene chloride (50 ml), washed with water (10 ml) and saline (10 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue is chromatographed on silica gel (230-400 mesh, 300 g; eluting with a gradient of ethyl acetate/hexane (10/90-50/50)) to give the title compound, C,H,N: Anal. Calcd for C20H27N3O1 : C=73.81, H=8.36, N=12.91-found: C=73.59, H=8.37, N=12.83.

Workup

  1. washwashed with water (10 ml) and saline (10 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed on silica gel (230-400 mesh, 300 g
  5. washeluting with a gradient of ethyl acetate/hexane (10/90-50/50))

Sources & evidence

ORD record
ord-f46c67e942b3493db6a54f5c40fb808f
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Linked notes

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