Hydrochloric Acid → HCID 11858312, compound

HRID 1710781Notes

Reaction equation

HRID 1710781 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16]Cl)=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[I-].[Na+].[CH3:27][CH:28]1[CH2:32][CH2:31][CH2:30][NH:29]1.Cl>C(#N)C>[Br:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][N:29]3[CH2:30][CH2:31][CH2:32][CH:28]3[CH3:27])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 130032-MethylpyrrolidineHCID 59457475HCID 59457475, compound

Product 1

HCID 11858312HCID 11858312, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1-[(5-bromo-2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl)methyl]piperidine i90 (0.39 g, 0.94 mmol, 1 eq) and 2-metlhylpyrrolidine (192 μl, 1.89 mmol, 2 eq) in acetonitrile (6 ml) is treated with sodium iodide (14 mg, 0.09 mmol, 0.1 eq) and stirred for 24 h at 90° C. 2-Methylpyrrolidine (100 μl, 1 mmol) is then added and the mixture is stirred for a further 24 h at 90° C. The mixture is then poured into 0.1 N hydrochloric acid (10 ml) and extracted with diethyl ether (10 ml). The aqueous phase is then treated with 1 N sodium hydroxide to reach pH 10 and extracted with dichloromethane (3×10 ml). The combined dichloromethane extracts are then dried over magnesium sulfate and concentrated to yield 370 mg of an orange oil which is purified by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96:3.6:0.4) to yield 86 mg of 1-[(5-bromo-2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)methyl]piperidine 117.

Workup

  1. stirringthe mixture is stirred for a further 24 h at 90° C
  2. extractionextracted with diethyl ether (10 ml)
  3. additionThe aqueous phase is then treated with 1 N sodium hydroxide
  4. extractionextracted with dichloromethane (3×10 ml)
  5. dry with materialThe combined dichloromethane extracts are then dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71d4f9d03de74627807b307ba1afa199
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

Loading…