Sodium Iodide → 1-(3-{4-[4-Methyl-5-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]phenoxy}propyl)piperidine

HRID 1710796Notes

Reaction equation

HRID 1710796 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([CH2:18][C:19]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(#N)C>[CH3:17][C:15]1[N:16]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:7][CH:8]=2)[S:13][C:14]=1[CH2:18][C:19](=[O:20])[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 594575031-({2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetyl)piperidine

Product 1

HCID 594574601-(3-{4-[4-Methyl-5-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]phenoxy}propyl)piperidineYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-({2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}acetyl)piperidine i104 (0.18 g, 0.51 mmol, 1 eq), potassium carbonate (0.14 g, 1.02 mmol, 2 eq) and sodium iodide (16 mg, 0.03 mmol, 0.2 eq) in acetonitrile (3 ml) is stirred at 80° C. for 20 minutes before addition of piperidine (0.15 ml, 0.51 mmol, 1.03 eq). The mixture is then stirred at reflux overnight, concentrated under vacuum and the residue is taken up in ethyl acetate (50 ml). The organic layer is washed with water (3×25 ml), brine, dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure to obtain an orange solid. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 90:10:1) affords 150 mg of 1-(3-{4-[4-methyl-5-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]phenoxy}propyl)piperidine 127.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated under vacuum
  3. washThe organic layer is washed with water (3×25 ml), brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure
  7. customto obtain an orange solid
  8. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 90:10:1)

Sources & evidence

ORD record
ord-fc79c09797704d99b150744d46f6c799
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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