Hydrochloric Acid → HCID 59457467, compound

HRID 1710767Notes

Reaction equation

HRID 1710767 reaction equation
CS(O[CH2:6][C:7]1[N:8]=[C:9]([Cl:12])[O:10][CH:11]=1)(=O)=O.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[I-].[Na+].Cl>C(#N)C>[Cl:12][C:9]1[O:10][CH:11]=[C:7]([CH2:6][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8082PiperidineHCID 59457456HCID 59457456, compound

Product 1

HCID 59457467HCID 59457467, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2-chloro-1,3-oxazol-4-yl)methyl methanesulfonate i59 (7.9 g, 37.44 mmol, 1 eq), piperidine (7.41 ml, 74.89 mmol, 2 eq) and sodium iodide (0.56 g, 3.74 mmol, 0.1 eq) in acetonitrile (250 ml) is stirred at room temperature overnight. The mixture is then poured into a 0.1 N hydrochloric acid solution and extracted with diethyl ether. The organic layer is dried over magnesium sulfate, filtered and the solvent is removed under reduced pressure. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 98:1.8:0.2) affords 3 g of 1-[(2-chloro-1,3-oxazol-4-yl)methyl]piperidine i60.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent is removed under reduced pressure
  5. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 98:1.8:0.2)

Sources & evidence

ORD record
ord-cb7ba42877844a1c9f901381762fb114
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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