1,3-Dibromopropane → 4-(3-Bromopropoxy)-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole

HRID 1384024Notes

Reaction equation

HRID 1384024 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[OH:6][C:7]1[C:15]2[N:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:12]([CH2:25][CH2:26][CH2:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)[C:11]=2[CH:10]=[CH:9][CH:8]=1>CN(C)C=O>[Br:1][CH2:2][CH2:3][CH2:4][O:6][C:7]1[C:15]2[N:14]=[C:13]([CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[N:12]([CH2:25][CH2:26][CH2:27][CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33]3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 211887714-Hydroxy-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole

Product 1

HCID 211884734-(3-Bromopropoxy)-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1,3-dibromopropane (41.3 mg, 0.3 mmol, 1.5 eq) in anhydrous N,N-dimethylformamide (2 ml) was treated with a solution of 4-hydroxy-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole (100 mg, 0.2 mmol, 1 eq) in anhydrous N,N-dimethylformamide (1 ml). The resulting mixture was stirred for twelve hours. The reaction was quenched by the addition of water (10 ml). The aqueous fraction was extracted with diethyl ether (3×10 ml). The organic fractions were combined, washed with water (3×10 ml), and brine (1×10 ml), and then dried over sodium sulfate. The solvents were removed in vacuo. The residue was subjected to column chromatography to yield the desired title product as a white crystalline product.

Workup

  1. customThe reaction was quenched by the addition of water (10 ml)
  2. extractionThe aqueous fraction was extracted with diethyl ether (3×10 ml)
  3. washwashed with water (3×10 ml), and brine (1×10 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-cf910e09245445a485fb7670ea79b9eb
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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