(3-Chloropropyl)benzene → HCID 21188518, compound

HRID 1384014Notes

Reaction equation

HRID 1384014 reaction equation
[CH2:1]([C:4]1[C:12]2[N:11]=[C:10]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:9]([CH2:22][CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[C:37]1([CH2:43][CH2:44][CH2:45]Cl)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O>[CH2:1]([C:4]1[C:12]2[N:11]=[C:10]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:9]([CH2:22][CH2:23][CH2:24][CH:25]3[CH2:26][CH2:27][N:28]([CH2:45][CH2:44][CH2:43][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:29][CH2:30]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7706(3-Chloropropyl)benzene2×HCID 11430Potassium Carbonate2×HCID 21188464HCID 21188464, compound

Product 1

HCID 21188518HCID 21188518, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In a 50 ml round bottom flask, under a nitrogen atmosphere, were added 4-(prop-2-enyl)-2-[(4-chlorophenoxy)methyl]-1-[3-(piperidin-4-yl)propyl]benzimidazole (898 mg, 2.12 mmol), potassium carbonate (1.46 g, 10.58 mmol), 3-(phenyl)propyl chloride (0.2 ml, 506 mg, 2.54 mmol) and N,N-dimethylformamide (7 ml). The resulting mixture was heated to 60° C. and maintained at this temperature overnight. The progress of the reaction was monitored by thin layer chromatography. An additional 1 equivalent of potassium carbonate and 0.2 ml of 3-(phenyl)propyl chloride were added and the resulting contents were stirred at 60° C. for an additional two hours. The reaction was quenched by the addition of water. The aqueous fraction was extracted wtih ethyl acetate. The organic fractions were combined, washed with water, and then dried over sodium sulfate. The solvents were removed in vacuo. The desired title product was further purified by radial chromatography.

Workup

  1. temperaturemaintained at this temperature overnight
  2. customThe reaction was quenched by the addition of water
  3. extractionThe aqueous fraction was extracted wtih ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customThe desired title product was further purified by radial chromatography

Sources & evidence

ORD record
ord-90a6d6c7c48141a0a386f0d476a7715c
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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