Triethylamine → 1-Benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine

HRID 361824Notes

Reaction equation

HRID 361824 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:22])[C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:24]1([O:27][CH2:28][CH3:29])[CH2:26][CH2:25]1.C(N(CC)CC)C>O1CCCC1.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:22])[C:15]2[C:20]([NH:21][C:24]3([O:27][CH2:28][CH3:29])[CH2:26][CH2:25]3)=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 106616501-Benzyl-4-[N-methyl-N-(3-amino-2-pyridinyl)amino]piperidineHCID 133803211-Bromo-1-ethoxycyclopropane

Product 1

HCID 106435211-Benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzyl-4-[N-methyl-N-(3-amino-2-pyridinyl)amino]piperidine (EXAMPLE 122, 825 mg), 1-bromo-1-ethoxycyclopropane (919 mg) and triethylamine (0.78 ml) in dry tetrahydrofuran (1.4 ml) under nitrogen is refluxed for 48 hrs, cooled to 20°-25°, diluted with methylene chloride (30 ml), washed with saline (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give the crude product. The residue is chromatographed (silica gel, 70-230 mesh, 140 g; eluting with a gradient of methanol/methylene chloride (1/99-5/95)) to give the title compound, NMR (CDCl3) 7.80, 7.41, 7.25, 6.93, 5.62, 3.51, 3.48, 3.03, 2.87, 2.60, 1.98, 1.71, 1.64, 1.13 and 0.85δ.

Workup

  1. temperatureis refluxed for 48 hrs
  2. temperaturecooled to 20°-25°
  3. washwashed with saline (10 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customThe residue is chromatographed (silica gel, 70-230 mesh, 140 g
  8. washeluting with a gradient of methanol/methylene chloride (1/99-5/95))

Sources & evidence

ORD record
ord-24bb735a9e6a41e986e4d7d6a9af0f11
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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