Ethanol → 7,6-Benzo-1,3-diazaspiro(4,5)decane-2,4-dione

HRID 1243155Notes

Reaction equation

HRID 1243155 reaction equation
[CH2:1]1[C:10](=O)[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[C-]#N.[Na+].[C:15](=[O:18])([O-])[O-].[NH4+:19].[NH4+:20].[CH2:21]([OH:23])C>O>[CH2:9]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][C:10]21[C:21](=[O:23])[NH:20][C:15](=[O:18])[NH:19]2

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 682662-TetraloneHCID 517111Ammonium Carbonate

Product 1

HCID 717267,6-Benzo-1,3-diazaspiro(4,5)decane-2,4-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred slurry of β-tetralone (3.3 mL, 25 mmol), sodium cyanide (1.84 g, 37.5 mmol), ammonium carbonate (14.26 g), absolute ethanol (50 mL) and water (50 mL) was heated to 80° C. for 48 hours. After cooling to room temperature, the reaction mixture was poured onto ice and stirred for 2 hours. The resulting precipitate was filtered and rinsed with water and dried under vacuum to provide the titled compound (5.28 g, 98%). 1H NMR (δ, DMSO-d6): 10.68 (s, 1H), 8.29 (s, 1H), 7.06–7.13 (m, 4H), 3.14 (d, 1H), 2.88–3.08 (m, 2H), 2.74 (d, 1H), 1.89–1.99 (m, 1H), 1.78–1.84 (m, 1H). MS (DCI/NH3): 234.1 (M+1).

Workup

  1. additionthe reaction mixture was poured onto ice
  2. filtrationThe resulting precipitate was filtered
  3. washrinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2596d74361e444f99df57655ec48c0d3
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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