Cyclopentylhydrazine hydrochloride → HCID 10545058, compound

HRID 612404

Reaction equation

HRID 612404 reaction equation
CO[C:3]1[C:4](=[O:21])[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](OC)[CH:14]=2)[CH2:6][CH2:7][C:8]=1[C:9](=O)[CH2:10][CH3:11].Cl.[CH:23]1([NH:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24]1.[CH3:30][O-:31].[Na+]>C(O)C>[CH:23]1([N:28]2[C:3]3[C:4](=[O:21])[N:5]([C:13]4[CH:14]=[CH:15][C:16]([O:31][CH3:30])=[CH:17][CH:18]=4)[CH2:6][CH2:7][C:8]=3[C:9]([CH2:10][CH3:11])=[N:29]2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 212349Cyclopentylhydrazine hydrochlorideHCID 10541431HCID 10541431, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10545058HCID 10545058, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 3-methoxy-1-(3-methoxyphenyl)-2-oxo-4-propionyl-1,2,5,6-tetrahydro-pyridine (0.49 grams, 1.7 mmole), cyclopentylhydrazine hydrochloride (0.40 grams) and sodium methoxide (46 mg, 0.85 mmole) in anhydrous ethanol was heated to reflux. After 16 hours, the mixture was concentrated under reduced pressure and chromatographed on a silica gel column using 1:4 ethyl acetate/hexane as eluent to give a white solid. Recrystallization from ether gave white needles. M.P. 64.65° C.; MS m/z [M+] 340.2025; HRMS [M+] 340.2046.

Workup

  1. temperaturewas heated to reflux
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customchromatographed on a silica gel column
  4. customto give a white solid
  5. customRecrystallization from ether
  6. customgave white needles

Sources & evidence

ORD record
ord-6d77ae71d4524779bbe1745cc5b103ac
Source dataset
uspto-grants-1999_12
Patent number
US06004974

Linked notes

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