Acetyl chloride → HCID 58387042, compound

HRID 1396126Notes

Reaction equation

HRID 1396126 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:27])[CH2:15][CH:16]([O:23][C:24](=[O:26])[NH2:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>O1CCCC1.O>[C:24]([O:23][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][C:35](=[O:37])[CH3:36])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1)=[O:27])(=[O:26])[NH2:25]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58387097HCID 58387097, compound

Product 1

HCID 58387042HCID 58387042, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound ‘carbamic acid 3-[4-(4-hydroxy-phenyl)-piperazin-1-yl]-3-oxo-1-phenyl-propyl ester (2 mmol)’ prepared in Example 18 was dissolved in tetrahydrofuran 25 mL), and triethylamine (2.4 mmol) and acetylchloride (2.4 mmol) were added to the mixture. The reslting mixture was stirred at a room temperature for 5 hours. Then, the reaction mixture was diluted with water, and extracted several times with ethyl acetate to obtain an organic phase. The prepared organic phase was dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1) to obtain a title compound.

Workup

  1. additionwere added to the mixture
  2. extractionextracted several times with ethyl acetate
  3. customto obtain an organic phase
  4. dry with materialThe prepared organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ed3c098db8864814930ee9d19a8fa854
Source dataset
uspto-grants-2014_12
Patent number
US08901116B2

Reaction notes

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