Diethyl Ether → HCID 59457472, compound

HRID 1710785Notes

Reaction equation

HRID 1710785 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][C:15]1[N:16]=[C:17]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][Cl:35])=[CH:27][CH:26]=2)[O:18][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(OCC)C>C(#N)C>[Cl:35][CH2:34][CH2:33][CH2:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:17]2[O:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:15]([CH2:14][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:16]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 59457461HCID 59457461, compound

Product 1

HCID 59457472HCID 59457472, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of piperidine (90 μl, 0.86 mmol, 1.1 eq) and potassium carbonate (0.43 g, 3 mmol, 4 eq) in acetonitrile (5 ml) is treated dropwise with a solution of ethyl 4-(bromomethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-oxazole-5-carboxylate i93 (0.30 g, 0.77 mmol, 1 eq) in acetonitrile (2 ml) and is stirred at room temperature overnight. Diethyl ether is then added and the solution is washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 210 mg of crude ethyl 2-[4-(3-chloropropoxy)phenyl]-4-(piperidin-1-ylmethyl)-1,3-oxazole-5-carboxylate i95, used as such in the next step.

Workup

  1. washthe solution is washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d5d3f81f58d4a6fbf9ece9c2ec9166e
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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