Acetyl chloride → HCID 67282031, compound

HRID 2408422Notes

Reaction equation

HRID 2408422 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][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:34](Cl)(=[O:36])[CH3:35]>O1CCCC1.O>[C:24]([O:23][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][C:34](=[O:36])[CH3:35])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1)(=[O:26])[NH2:25]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67280963HCID 67280963, compound

Product 1

HCID 67282031HCID 67282031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound ‘carbamic acid 3-[4-(4-hydroxy-phenyl)-piperazin-1-yl]-1-phenyl-propyl ester (2 mmol) prepared in Example 84 was dissolved in tetrahydrofuran (25 mL), and triethylamine (2.4 mmol) and acetylchloride (2.4 mmol) were added thereto, and the resulting mixture was 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-fa01186ffb4a4f4aadc324d325c06a07
Source dataset
uspto-grants-2014_08
Patent number
US08815852B2

Reaction notes

Loading…