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

HRID 1911139Notes

Reaction equation

HRID 1911139 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-12d4248ab01948f0b8daea20c069a125
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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