Potassium Hydroxide → 2-Butyl-1,3-diazaspiro(4.4)non-1-en-4-one hydrochloride
Reaction equation
[C:1]([C:3]1([NH:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[OH-:15].[K+].[Cl-:17].[NH4+]>CO.O>[ClH:17].[CH2:10]([C:9]1[NH:2][C:1](=[O:15])[C:3]2([CH2:7][CH2:6][CH2:5][CH2:4]2)[N:8]=1)[CH2:11][CH2:12][CH3:13]Participants
Conditions
- Temperature
- 55 °C
Procedure
To 19.6 g (0.1 mol) of 1-cyano-1-n-pentanoylaminocyclopentane dissolved in 70 ml of methanol, 25 g (0,46 mol) of potassium hydroxide dissolved in 50 ml of water was added. The resulting solution was stirred and heated at 50-60° C., then under reflux conditions for 2,5 hours. The pH was decreased by the addition of 25 g of ammonium chlorid, then methanol was distilled off. The residue was extracted with 50 ml and 2×30 ml of toluene, the combined organic phases were evaporated to constant weight The residual 16 g of title compound was dissolved in 100 ml of acetone, the pH of the resulting solution was adjusted to 1-2 with hydrochloric acid solution, the mixture was crystallized, the crystals were collected by filtration to obtain 14 g of the title compound, yield 60.8%.
Workup
- additionwas added
- waitunder reflux conditions for 2,5 hours
- distillationmethanol was distilled off
- extractionThe residue was extracted with 50 ml and 2×30 ml of toluene
- customthe combined organic phases were evaporated to constant weight The residual 16 g of title compound
- dissolutionwas dissolved in 100 ml of acetone
- customthe mixture was crystallized
- filtrationthe crystals were collected by filtration
Sources & evidence
- ORD record
- ord-ecc3c624db6a4d6dbb7559dbd80c9c89
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211382B1
Reaction notes
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