Potassium Cyanide → HCID 66599950, compound

HRID 1621725Notes

Reaction equation

HRID 1621725 reaction equation
[C-]#N.[K+].[C:4](=[O:7])([O-])[O-].[NH4+:8].[NH4+:9].[CH:10]([N:23]1[CH2:26][C:25](=O)[CH2:24]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[CH2:29][OH:30].O>>[CH:10]([N:23]1[CH2:26][C:25]2([C:29](=[O:30])[NH:9][C:4](=[O:7])[NH:8]2)[CH2:24]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 19096565Water ethanol

Product 1

HCID 66599950HCID 66599950, compoundYield 43.7%

Conditions

Temperature
60 °C

Procedure

Potassium cyanide (0.151 g, 2.32 mmol), ammonium carbonate (0.445 g, 4.64 mmol), and 1-benzhydrylazetidin-3-one (WO2007109334) (0.500 g, 2.11 mmol) were combined in 10 mL 2:1 EtOH/H2O and heated at 60° C. for 3 days in a sealed tube. The reaction mixture was cooled and concentrated in vacuo to remove EtOH. Additional water was added, and the solids were collected by filtration, rinsing with water and a minimal volume of MeOH. This gave 441 mg of a white solid. The material was suspended in 10 mL MeOH and sonicated for 10 min. The solid was collected and rinsed with MeOH to give 2-benzhydryl-2,5,7-triazaspiro[3.4]octane-6,8-dione (0.283 g, 43.7% yield) as a white solid. m/z (ESI, +ve ion) 308.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customto remove EtOH
  4. additionAdditional water was added
  5. filtrationthe solids were collected by filtration
  6. washrinsing with water
  7. customsonicated for 10 min
  8. customThe solid was collected
  9. washrinsed with MeOH

Sources & evidence

ORD record
ord-7bf4351ee5b243eda5241fe4c4ba1b42
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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