Sodium Hydroxide → 2,8-Diazaspiro[4.5]decan-1-one, 4-(4-fluorophenyl)-

HRID 2274982Notes

Reaction equation

HRID 2274982 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:13]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:12](=[O:19])[NH:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-].[Na+]>CCOC(C)=O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:13]3([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[C:12](=[O:19])[NH:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 497593214-(4-Fluorophenyl)-2,8-diazaspiro[4.5]decan-1-one hydrochloride

Product 1

HCID 116391192,8-Diazaspiro[4.5]decan-1-one, 4-(4-fluorophenyl)-Yield 316.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3.5 g (3.5 mmol) of 4-(4-fluorophenyl)-2,8-diazaspiro[4.5]decan-1-one hydrochloride was added EtOAc and 10% aqueous NaOH until dissolution occurred. The layers were separated and the aqueous layer was further extracted with ethyl acetate and DCM. The combined organic layers were dried over MgSO4 and filtered. The solvents were removed under reduced pressure to give 2.75 g (90%) of 4-(4-fluorophenyl)-2,8-diazaspiro[4.5]decan-1-one as a foamy white solid: 1HNMR (400 MHz, DMSO-d6) δ ppm 7.73 (s, 1H), 7.29 (d, 1H, J=8.4 Hz), 7.28 (d, 1H, J=8.4 Hz), 7.16-7.11 (m, 2H), 3.53 (dd, 1H, J=10.4 and 7.8), 3.37-3.26 (m, 4H), 3.05-3.01 (m, 1H), 2.73-2.67 (m, 1H), 2.64-2.59 (m, 1H), 2.32-2.26 (m, 3H), and 1.52-1.43 (m, 1H); LCMS m/z: 249.2 (M+H)+.

Workup

  1. dissolutionuntil dissolution
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with ethyl acetate and DCM
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-c78e44ffbbe843e19cbc853bc34486ed
Source dataset
uspto-grants-2015_09
Patent number
US09127005B2

Reaction notes

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