Sodium Iodide → HCID 11857307, compound

HRID 1710736Notes

Reaction equation

HRID 1710736 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17]Cl)=[CH:10][CH:9]=2)[O:6][CH:7]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:27][CH:28]1[CH2:32][CH2:31][CH2:30][NH:29]1.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C(#N)C>[CH3:27][CH:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:10][CH:9]=2)[O:6][CH:7]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457464HCID 59457464, compound

Product 1

HCID 11857307HCID 11857307, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(chloromethyl)-2-[4-(3-chloropropoxy)phenyl]-1,3-oxazole ax57 (0.172 g, 0.6 mmol, 1 eq), sodium iodide (0.018 g, 0.12 mmol, 0.2 eq), potassium carbonate (0.373 g, 2.7 mmol, 4.5 eq) and 2-methylpyrrolidine in acetonitrile (5 ml) is stirred at room temperature for 72 h. Piperidine (0.05 g, 0.6 mmol, 1 eq) is then added and the mixture is stirred at 80° C. overnight. The volatiles are then removed under vacuum and the residue is purified by chromatography (dichloromethane/methanol/ammonia 96:3.6:0.4) to give 1-[3-(4-{4-[(2-methylpyrrolidin-1-yl)methyl]-1,3-oxazol-2-yl}phenoxy)propyl]piperidine 30 as a pale yellow oil.

Workup

  1. stirringthe mixture is stirred at 80° C. overnight
  2. customThe volatiles are then removed under vacuum
  3. customthe residue is purified by chromatography (dichloromethane/methanol/ammonia 96:3.6:0.4)

Sources & evidence

ORD record
ord-994709cefe2e484299756834d120dab5
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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