Butyl iodide → 1-(6-Amino-2-methoxy-3-pyridinyl)-3-(1-butyl-4-piperidinyl)-1-propanone

HRID 489798Notes

Reaction equation

HRID 489798 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1.I[CH2:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:19])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 222626571-(6-Amino-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone

Product 1

HCID 222625941-(6-Amino-2-methoxy-3-pyridinyl)-3-(1-butyl-4-piperidinyl)-1-propanoneYield 50.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(6-amino-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone (step 1, 175 mg, 0.665 mmol), 1-iodobutane (0.083 ml, 0.732 mmol) and potassium carbonate (184 mg, 1.33 mmol) in tetrahydrofuran (5 ml) was refluxed for 6 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (50 ml), washed with water (5 ml) and brine (10 ml) and dried over potassium carbonate. Removal of solvent gave the pale yellow oil, which was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.2:1:10) to give pale yellow solid, which was washed with acetonitrile to afford 107.0 mg (50%) of the title compound as pale yellow solids.

Workup

  1. temperaturewas refluxed for 6 h
  2. washwashed with water (5 ml) and brine (10 ml)
  3. dry with materialdried over potassium carbonate
  4. customRemoval of solvent
  5. customgave the pale yellow oil, which
  6. customwas chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (0.2:1:10)
  7. customto give pale yellow solid, which
  8. washwas washed with acetonitrile

Sources & evidence

ORD record
ord-03a82c762b644ea29fad7de1d023748c
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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