Acetyl chloride → 4-(4-Methylpiperazin-1-yl)phenyl acetate

HRID 45807

Reaction equation

HRID 45807 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:15](Cl)(=[O:17])[CH3:16]>C(Cl)Cl>[C:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:9][CH:10]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 116224864-(4-Methyl-1-piperazinyl)phenol

Product 1

HCID 679737964-(4-Methylpiperazin-1-yl)phenyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-methylpiperazin-1-yl)phenol 1.080 mg (5.59 mmol) and TEA 1.72 ml (12.3 mmol) in DCM was cooled in an ice bath and 0.44 ml (6.15 mmol) of acetyl chloride were added dropwise. After completion, the reaction was filtered, the organic phase quickly extracted with water, dried over Na2SO4 and evaporated down to give a light pink solid. LC/MS (m/z): 235.4 [M+H]+, HPLC (254 nm) method 3 Rt 1.89 min.

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationAfter completion, the reaction was filtered
  3. extractionthe organic phase quickly extracted with water
  4. dry with materialdried over Na2SO4
  5. customevaporated down
  6. customto give a light pink solid

Sources & evidence

ORD record
ord-ceedaa7f8b0344ddb93c9ecc488533c5
Source dataset
uspto-grants-2013_09
Patent number
US08541576B2

Linked notes

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