Acetyl chloride → HCID 66751022, compound

HRID 534953Notes

Reaction equation

HRID 534953 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27].C(=O)([O-])O.[Na+]>C1COCC1>[C:26]([N:16]1[CH2:17][CH2:18][N:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:3]([CH3:6])([CH3:4])[CH3:5])[CH2:14][CH2:15]1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751022HCID 66751022, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1 (2 tert-butylphenyl)piperazine dihydrochloride (29 mg, 0.1 mmol) and triethylamine (0.021 mL, 0.3 mmol) in THF (1.0 mL) was added acetyl chloride (23 mg, 0.3 mmol) at rt. After stirring for 2 h at room temperature, saturated sodium hydrogen carbonate solution (1.5 mL) was added to the mixture, and the mixture was extracted with ethyl acetate (2 mL). The organic layer was separated by phase separation filter kit and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in DMSO (1 mL) and the solution was purified by preparative HPLC. The eluted fraction was evaporated by air blowing at 60° C. to give a title compound (20.5 mg, 79%). LC/MS (ESI+) m/z 261 [M+H], purity 100%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2 mL)
  2. customThe organic layer was separated by phase separation
  3. filtrationfilter kit
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in DMSO (1 mL)
  6. customthe solution was purified by preparative HPLC
  7. customThe eluted fraction was evaporated by air
  8. customblowing at 60° C.

Sources & evidence

ORD record
ord-e729cba512bc4b6d87e027e0098efe79
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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