Triethylamine → HCID 67138121, compound

HRID 1295978Notes

Reaction equation

HRID 1295978 reaction equation
[C:1]([O:4][CH2:5][C:6](Cl)=[O:7])(=[O:3])[CH3:2].[Br:9][C:10]1[CH:11]=[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:13]([O:22][CH3:23])=[C:14]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]([N:19]1[CH2:18][CH2:17][N:16]([C:14]2[CH:15]=[C:10]([Br:9])[CH:11]=[C:12]([C:24]([CH3:25])([CH3:27])[CH3:26])[C:13]=2[O:22][CH3:23])[CH2:21][CH2:20]1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 589099601-(5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine

Product 1

HCID 67138121HCID 67138121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetoxyacetyl chloride (0.14 ml) was added to a solution of 1-[5-bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine (360 mg) and triethylamine (0.31 ml) in CH2Cl2 (5 ml) while cooling on ice and the mixture was brought to room temperature and stirred for 1 hour. After quenching the reaction with brine, extraction was performed with ethyl acetate to yield a crude product of 2-{4-[5-bromo-3-(tert-butyl)-2-methoxyphenyl]piperazino}-2-oxoethyl acetate as a red oil. This crude product was dissolved in methanol (2.5 ml) and potassium carbonate (167 mg) was added. After 15 minutes, brine was added, extraction was performed with ethyl acetate, the extract was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (285 mg) as light orange crystals (67%).

Workup

  1. temperaturewhile cooling on ice
  2. customwas brought to room temperature
  3. customAfter quenching
  4. customthe reaction
  5. extractionwith brine, extraction

Sources & evidence

ORD record
ord-68ed802f23ef4ddd88c992f39dcf9e51
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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