Potassium Carbonate → 9-(1-(4-Bromo-2-fluorophenyl)ethyl)-4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

HRID 1525865Notes

Reaction equation

HRID 1525865 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])=[C:26]([F:33])[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])=[C:26]([F:33])[CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69083351HCID 69083351, compoundHCID 829694964-Bromo-1-(1-bromoethyl)-2-fluorobenzene

Product 1

HCID 712707719-(1-(4-Bromo-2-fluorophenyl)ethyl)-4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-oneYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (2.483 mmol) in N,N-dimethylformamide (10 mL) was treated with potassium carbonate (7.45 mmol) and 4-bromo-1-(1-bromoethyl)-2-fluorobenzene (2.483 mmol). The reaction was stirred at room temperature for three days. The solution was diluted with water (200 mL) and was extracted three times with ethyl acetate. The organic layers were combined, washed with brine (five times), dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a yellow oil (1.01 g, 89%). MS(ES)+ m/e 411.0/412.9 [M+H]+ (bromide isotope pattern).

Workup

  1. extractionwas extracted three times with ethyl acetate
  2. washwashed with brine (five times)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8d367901d364514a564ab0290254666
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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