Water → HCID 57656617, compound

HRID 911606Notes

Reaction equation

HRID 911606 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5]1([C:11]([C:13]2[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=2)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.O>CN(C=O)C>[N:1]([CH2:17][C:16]1[CH:19]=[CH:20][C:13]([C:11]([CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[O:12])=[CH:14][CH:15]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 57656437HCID 57656437, compound

Product 1

HCID 57656617HCID 57656617, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Add sodium azide (441 mg, 6.785 mmol) to a stirred solution of 4-(cyclohexanecarbonyl)-benzyl bromide (954 mg, 3.393 mmol) in anhydrous DMF (20 mL) and heat the mixture to 90° C. for 2 h. Cool the mixture to room temperature, add water and extract the aqueous solution with diethyl ether. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1) to give the desired intermediate as oil (310 mg, 38%).

Workup

  1. temperatureCool the mixture to room temperature
  2. extractionextract the aqueous solution with diethyl ether
  3. dry with materialDry the combined organic extracts over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1)

Sources & evidence

ORD record
ord-66a131225ac049768141cea86716d129
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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