3,3-Dimethyl-1-butyne → HCID 58996662, compound

HRID 1592744Notes

Reaction equation

HRID 1592744 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][N:21]=[N+:22]=[N-:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C:25]([CH3:29])([CH3:28])[C:26]#[CH:27]>C1(C)C=CC=CC=1>[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][N:21]2[CH:27]=[C:26]([C:25]([CH3:29])([CH3:28])[CH3:24])[N:23]=[N:22]2)[CH2:10][CH2:9]1)([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

4

Reactant 2

HCID 135123,3-Dimethyl-1-butyneHCID 17952251HCID 17952251, compound

Product 1

HCID 58996662HCID 58996662, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a sealed tube, 4-(2-Azidomethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.366 g, 1.15 mmol) was dissolved in toluene (5 mL). 3,3-dimethyl-1-butyne (0.7 mL, 5.64 mmol) was added and the mixture was heated to reflux for about 48 hours and then cooled to r.t. The mixture was concentrated under reduced pressure and purified using silica chromatography (50% ethyl acetate in hexanes) to give the title compound (0.212 g, 60%) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 48 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-4f1eb95ba9cf40de9759b29040c0ac75
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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