Acetyl chloride → HCID 67281860, compound

HRID 2408427Notes

Reaction equation

HRID 2408427 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:24][C:25](=[O:27])[NH2:26])[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>CC(C)=O.O>[C:25]([O:24][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:35](=[O:37])[CH3:36])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)(=[O:27])[NH2:26]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67280973HCID 67280973, compound

Product 1

HCID 67281860HCID 67281860, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The compound ‘carbamic acid 1-(4-fluoro-phenyl)-3-[4-(4-hydroxy-phenyl)-piperazin-1-yl]-propyl ester (0.6 mmol) prepared in Example 88 was dissolved in acetone (15 mL), and triethylamine (1.2 mmol) was added and acetylchloride (2.4 mmol) was added dropwise, and the resulting mixture was then stirred at a room temperature for 5 hours. 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. extractionextracted several times with ethyl acetate
  2. customto obtain an organic phase
  3. dry with materialThe prepared organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e7373ac9f6614808864179d508b5210c
Source dataset
uspto-grants-2014_08
Patent number
US08815852B2

Reaction notes

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