Hydrochloric Acid → HCID 10302076, compound

HRID 895339Notes

Reaction equation

HRID 895339 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH:15]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16][O:17][CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[CH2:11][CH2:10]1)C.C(O)C.[OH-].[Na+].Cl>O>[F:28][C:25]([F:26])([F:27])[C:23]1[CH:24]=[C:19]([CH:20]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:22]=1)[CH2:18][O:17][CH2:16][CH:15]([N:12]1[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:39])=[O:3])[CH2:14][CH2:13]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86590284HCID 86590284, compound2×

Product 1

HCID 10302076HCID 10302076, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

In a round-bottomed flask fitted with a reflux condenser and a thermometer 2.48 g (4 mmoles) of 5-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-pentanoic acid ethyl ester (compound 140 prepared at example 1.4.1 above), 45 ml of ethyl alcohol, 4 ml of water, and 6.6 ml of a 1N solution of sodium hydroxide in water were introduced. The mixture was stirred at room temperature for 22 hours, and 6.6 ml of a 1N solution of hydrochloric acid in water was added. The volatile substances were removed under reduced pressure, water and methylene chloride were added, the aqueous layer was extracted with methylene chloride, and the combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in 35 ml of methylene chloride, 3.96 ml of a 1.96 N solution of hydrochloric acid in diethyl ether were added, and the volatile substances were removed under reduced pressure. The residue was recristallized from acetonitrile, affording 1.6 g of 5-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-pentanoic acid (compound 233) as a solid. Yield: 61%.

Workup

  1. customIn a round-bottomed flask fitted with a reflux condenser
  2. customThe volatile substances were removed under reduced pressure, water and methylene chloride
  3. additionwere added
  4. extractionthe aqueous layer was extracted with methylene chloride
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 35 ml of methylene chloride
  8. addition3.96 ml of a 1.96 N solution of hydrochloric acid in diethyl ether were added
  9. customthe volatile substances were removed under reduced pressure

Sources & evidence

ORD record
ord-16d8ae08bdf64b4b920b5725ceed368c
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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