Sodium Iodide → HCID 21262755, compound

HRID 567786Notes

Reaction equation

HRID 567786 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[C:17]1([CH2:23][CH2:24]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O.O>[CH2:24]([N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[O:16])[CH2:5][CH2:6]1)[CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Product 1

HCID 21262755HCID 21262755, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-piperidin-4-yl-1,3-dihydro-benzimidazol-2-one (0.5 g, 2.3 mmol), 2-phenyl-ethylbromid (0.34 ml, 2.5 mmol), triethylamine (0.35 ml, 2.5 mmol) and sodium iodide (0.01 g, 0.67 mmol) in dry N,N-dimethyl foramide (5 ml) was stirred at 100° C. for 3 hours. The reaction mixture was cooled to room temperature, and then poured into water (20 ml). The product precipitated upon stirring on a ice/water bath and was isolated by filtration. Yield 0.45 g (1.4 mmol, 61%). M.p. 181-185° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe product precipitated
  3. stirringupon stirring on a ice/water bath
  4. customwas isolated by filtration

Sources & evidence

ORD record
ord-ba3599eeb2b04b228df1fa9c8f528871
Source dataset
uspto-grants-2001_01
Patent number
US06180649B2

Reaction notes

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