Acetyl chloride → 1-{4-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazino}-1-ethanone

HRID 1295977Notes

Reaction equation

HRID 1295977 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:9]([O:18][CH3:19])=[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:11]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:9]([O:18][CH3:19])=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:1](=[O:3])[CH3:2])[CH2:16][CH2:17]2)[CH:11]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 589099601-(5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine

Product 1

HCID 589099951-{4-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazino}-1-ethanoneYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetyl chloride (0.10 ml) was mixed with a solution of 1-[5-bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine (370 mg) and triethylamine (0.32 mL) in methylene chloride (8 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and, after filtering off the insoluble portion, was concentrated. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (338 mg) as colorless crystals (81%).

Workup

  1. filtrationafter filtering off the insoluble portion
  2. concentrationwas concentrated
  3. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-fc53ad246b67416bbc5f32affe9fb1e8
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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