Potassium Carbonate → 9-(1-(4-Bromophenyl)ethyl)-4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

HRID 1525862Notes

Reaction equation

HRID 1525862 reaction equation
Cl.[CH:2]1([N:5]2[CH2:10][C:9]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[O:8][CH2:7][C:6]2=[O:16])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30](Br)[CH3:31])=[CH:26][CH:25]=1>CN(C)C=O.O>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([N:13]2[CH2:12][CH2:11][C:9]3([O:8][CH2:7][C:6](=[O:16])[N:5]([CH:2]4[CH2:4][CH2:3]4)[CH2:10]3)[CH2:15][CH2:14]2)[CH3:31])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 98381461-Bromo-4-(1-bromoethyl)benzeneHCID 69083351HCID 69083351, compound

Product 1

HCID 712708649-(1-(4-Bromophenyl)ethyl)-4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (0.341 mmol) in N,N-dimethylformamide (1.5 mL) was treated with potassium carbonate (0.682 mmol) and 1-bromo-4-(1-bromoethyl)benzene (0.341 mmol). The reaction mixture was stirred at room temperature overnight. The solution was diluted with water (50 mL) and was extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a brown residue (117 mg, 87%). MS(ES)+ m/e 392.9/394.7 [M+H]+ (bromide isotope pattern).

Workup

  1. extractionwas extracted three times with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d72dd86c7e84953ab37b3b9a369ac35
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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