Ammonia → 2-Butyl-1,3-diaza-spiro[4.4]nonan-4-one

HRID 1636978Notes

Reaction equation

HRID 1636978 reaction equation
N.[NH2:2][C:3]1([C:8]([NH2:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH3:15].CC(CC(C)=O)C>O>[CH2:12]([CH:11]1[NH:10][C:8](=[O:9])[C:3]2([CH2:7][CH2:6][CH2:5][CH2:4]2)[NH:2]1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7909Methyl Isobutyl KetoneHCID 8063PentanalHCID 111160861-Aminocyclopentanecarboxamide

Product 1

HCID 101980702-Butyl-1,3-diaza-spiro[4.4]nonan-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Ammonia solution (20%; 20 g, 0.30 mol.) is added to a solution of 126 g of 1-aminocyclopentanecarboxamide (>98%, 0.98 mol.) in 150 g of water. 86 g of valeraldehyde (0.99 mol.) are then added at 15° C., during which the temperature rises to 32° C. The reaction mixture is heated to 70° C. and stirred for 7 hours at that temperature. 350 ml of MIBK are added to the emulsion, and the mixture is cooled, with stirring, and the organic phase is separated off. The extract is extensively concentrated by evaporation (200 g), and 200 g of n-hexane are added, and the crystals are filtered off. After drying there remain 125 g of 2-butyl-1,3-diaza-spiro [4.4]nonan4-one (HPLC: 98.6%).

Workup

  1. customrises to 32° C
  2. temperaturethe mixture is cooled
  3. stirringwith stirring
  4. customthe organic phase is separated off
  5. concentrationThe extract is extensively concentrated by evaporation (200 g), and 200 g of n-hexane
  6. additionare added
  7. filtrationthe crystals are filtered off
  8. dry with materialAfter drying there remain 125 g of 2-butyl-1,3-diaza-spiro [4.4]nonan4-one (HPLC: 98.6%)

Sources & evidence

ORD record
ord-d8e2b96eff55487aafbe579078c77b78
Source dataset
uspto-grants-2000_03
Patent number
US06037474

Reaction notes

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