Hydrazine hydrate (1:1) → HCID 68495857, compound

HRID 1798944Notes

Reaction equation

HRID 1798944 reaction equation
CC1C=C(C2C=CC(C3CCNCC3)=NC=2)C=CN=1.O.[NH2:21][NH2:22].[CH:23]([N:26]1[CH2:31][CH2:30][CH:29]([C:32](=O)[CH2:33][CH:34](N2CCOCC2)[C:35]([OH:37])=O)[CH2:28][CH2:27]1)([CH3:25])[CH3:24]>CC(O)CC>[CH:23]([N:26]1[CH2:27][CH2:28][CH:29]([C:32]2[CH:33]=[CH:34][C:35](=[O:37])[NH:21][N:22]=2)[CH2:30][CH2:31]1)([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 59543416HCID 59543416, compoundHCID 68496108HCID 68496108, compound

Product 1

HCID 68495857HCID 68495857, compound

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

In analogy to Wermuth et al. in J. Med. Chem. 1987, 30 (2), 246, hydrazine hydrate (10 mL) was added to a solution of 4-(1-isopropylpiperidin-4-yl)-2-morpholin-4-yl-4-oxo-butyric acid (99.9 g, 0.25 mol) in 2-butanol (500 mL). The reaction mixture was stirred at room temperature for 1 h followed by reflux overnight. After cooling to room temperature the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (SiO2, dichloromethane with 3% methanol followed by 5% and 7%.). Evaporation of the fractions containing the desired product yielded a yellow solid, which was used as such.

Workup

  1. temperatureby reflux overnight
  2. temperatureAfter cooling to room temperature the solvent
  3. customwas evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography (SiO2, dichloromethane with 3% methanol followed by 5% and 7%.)
  5. customEvaporation of the fractions
  6. additioncontaining the desired product
  7. customyielded a yellow solid, which

Sources & evidence

ORD record
ord-57d041cd7f47428793c5fb7689982cb9
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

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