Hydrochloric Acid → HCID 58237158, compound

HRID 2199445Notes

Reaction equation

HRID 2199445 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:21][CH2:20][C:10]3([CH2:19][CH2:18][CH2:17][C:12]4(OCC[O:13]4)[CH2:11]3)[C:9]2=[O:22])[CH:5]=[CH:6][CH:7]=1.C1COCC1.Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:21][CH2:20][C:10]3([CH2:19][CH2:18][CH2:17][C:12](=[O:13])[CH2:11]3)[C:9]2=[O:22])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 58237325HCID 58237325, compound

Product 1

HCID 58237158HCID 58237158, compoundYield 162.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 9-(3-chloro-phenyl)-1,4-dioxa-9-aza-dispiro[4.1.4.3]tetradecan-8-one from step 4 (0.45 g, 0.84 mmol), THF (10.2 mL), and 2N aqueous HCl (7.0 mL). After stirring at rt overnight, the reaction mixture was diluted with ethyl acetate (60 mL). The organic layer was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to afford 0.38 g (97%) of the title compound, 2-(3-chloro-phenyl)-2-aza-spiro[4.5]decane-1,7-dion, as a white solid, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ7.74 (t, J=2.0 Hz, 1H), 7.52 (ddd, J=8.3, 2.2, 1.0 Hz, 1H), 7.29 (t, J=8.1 Ha, 1H), 7.13 (ddd, J=8.1, 2.0, 1.0 Hz, 1H), 3.72-3.81 (m, 2H), 2.73 (dd, J=13.9, 1.0 Hz, 1H), 2.35-2.50 (m, 2H), 2.29 (dt, J=13.9, 1.7 Hz, 1H), 2.12-2.22 (m, 2H), 2.02-2.07 (m, 2H), 1.71-1.89 (m, 2H). ESI-MS m/z: 278 (M+H)+.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba7a953ef000466e9a897eef0543ce0a
Source dataset
uspto-grants-2016_06
Patent number
US09359297B2

Reaction notes

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