Sodium Hydroxide → HCID 18430872, compound

HRID 1278617Notes

Reaction equation

HRID 1278617 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([NH:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=O)[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CCN=C=NCCCN(C)C>O1CCOCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([N:21]3[CH2:22][CH2:23][CH2:24][C:25]3=[O:27])[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18430859HCID 18430859, compound

Product 1

HCID 18430872HCID 18430872, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4-[[1-[2-(4-benzyl-1-piperazinyl)ethyl]cyclopentyl]amino]butanoate (333 mg/0.83 mmol) and 2 N—NaOH (1.3 ml/2.6 mmol) in dioxane (6 ml) was stirred for 8 hours at 80° C., and then the mixture was acidified with sat.NaH2PO4 (10 ml). The mixture was concentrated in vacuo. The residue was suspended in dichloromethane-methanol (5:1, 30 ml) and the mixture was refluxed for 1 hour. After filtration, the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane (20 ml). To the mixture was added WSC (431 mg/2.25 mmol) and the mixture was refluxed for 2 d. After cooling to room temperature, the mixture was washed with water (10 ml×2). The combined extracts were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si, 230-400 mesh/dichloromethane:methanol=30:1-15:1) to give a yellow oil (150 mg/ 51%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. temperaturethe mixture was refluxed for 1 hour
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  6. temperaturethe mixture was refluxed for 2 d
  7. temperatureAfter cooling to room temperature
  8. washthe mixture was washed with water (10 ml×2)
  9. washThe combined extracts were washed with brine (10 ml)
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by column chromatography (Si, 230-400 mesh/dichloromethane:methanol=30:1-15:1)
  14. customto give a yellow oil (150 mg/ 51%)

Sources & evidence

ORD record
ord-6e9acc79a4c84e508711b866532f2e96
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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