Hydrochloric Acid → 4-({3-[4-(Phenylcarbonyl)piperazin-1-yl]azetidin-1-yl}carbonyl)phenol

HRID 1023075Notes

Reaction equation

HRID 1023075 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:16][CH:15]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:24])[CH2:19][CH2:18]3)[CH2:14]2)=[O:12])=[CH:7][CH:6]=1)(=O)C.[Li+].[OH-].Cl>C1COCC1.CO.O>[C:25]1([C:23]([N:20]2[CH2:21][CH2:22][N:17]([CH:15]3[CH2:16][N:13]([C:11]([C:8]4[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=4)=[O:12])[CH2:14]3)[CH2:18][CH2:19]2)=[O:24])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 596259394-({3-[4-(Phenylcarbonyl)piperazin-1-yl]azetidin-1-yl}carbonyl)phenyl acetate

Product 1

HCID 596258104-({3-[4-(Phenylcarbonyl)piperazin-1-yl]azetidin-1-yl}carbonyl)phenol

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of compound 26c (420 mg, 1.03 mmol) and LiOH (100 mg, 4.0 mmol) in a solvent mixture of THF/MeOH/H2O (2/2/2 mL) was stirred at room temperature for 4 h, at which time it was brought to pH 5 by the addition of 2N HCl (aq). The mixture was extracted with EtOAc (3×). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The resultant residue (crude compound 26d) was dried under reduced pressure for 18 h, and used in the following step without further purification.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dry with materialThe resultant residue (crude compound 26d) was dried under reduced pressure for 18 h
  6. customused in the following step without further purification

Sources & evidence

ORD record
ord-7921c513197b4bde80787aada1eab474
Source dataset
uspto-grants-2014_05
Patent number
US08722658B2

Reaction notes

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