Sodium Iodide → HCID 11858392, compound

HRID 1710771Notes

Reaction equation

HRID 1710771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][CH:15]=[C:16]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11]Cl.[CH3:25][CH:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:14][CH:15]=[C:16]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH3:25]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 130032-MethylpyrrolidineHCID 59457458HCID 59457458, compound

Product 1

HCID 11858392HCID 11858392, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-({2-[3-chloro-4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}methyl)piperidine i71 (0.12 g, 0.32 mmol, 1 eq) and 2-methylpyrrolidine (63 PI, 0.65 mmol, 2 eq) in acetonitrile (10 ml) is treated with sodium iodide (5 mg, 0.03 mmol, 0.1 eq) and stirred at room temperature overnight. The mixture is then washed with water, dried over magnesium sulfate, and concentrated to give the crude product. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 90:10:0.1) gives 75 mg of 1-[(2-{3-chloro-4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)methyl]piperidine 124 as an orange oil.

Workup

  1. washThe mixture is then washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 90:10:0.1)

Sources & evidence

ORD record
ord-5adbac9f90604f80b8900971a9c43c5c
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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