4-Bromobenzyl bromide → HCID 21914355, compound

HRID 2421362Notes

Reaction equation

HRID 2421362 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][O:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][O:11][CH3:10])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 27346381-(2-Methoxyethyl)piperazine

Product 1

HCID 21914355HCID 21914355, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromobenzyl bromide (2.0 g) and 1-(2-methoxyethyl)piperazine (2.31 g) were stirred in dimethylformamide (30 ml) for 18 h. The mixture was partitioned between diethyl ether (30 ml) and water (30 ml). The aqueous phase was extracted further with ether (30 ml) and the combined organics were washed with water (50 ml), dried (MgSO4), concentrated in vacuo and purified by Bondelute® chromatography, eluting with 0-100% ethyl acetate/iso-hexane followed by 10-50% methanol/ethyl acetate to give the product as a yellow oil (1.61 g).

Workup

  1. customThe mixture was partitioned between diethyl ether (30 ml) and water (30 ml)
  2. extractionThe aqueous phase was extracted further with ether (30 ml)
  3. washthe combined organics were washed with water (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by Bondelute® chromatography
  7. washeluting with 0-100% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-d2914393b1514528ae09e4928bbe5613
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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