Isobutyl iodide → HCID 17952317, compound

HRID 1592762Notes

Reaction equation

HRID 1592762 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:27](I)[CH:28]([CH3:30])[CH3:29]>CN(C=O)C.CCOC(C)=O>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate

Product 1

HCID 17952317HCID 17952317, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-Boc-4-(2-hydroxy-phenyl)-piperazine (560 mg, 2.0 mmol) in 10 mL of DMF was added K2CO3 (835 mg, 6 mmol). After stirring for about 5 minutes, isobutyl iodide (350 uL, 3 mmol) was added. After stirring overnight at 60° C., the solution was warmed to about 80° C. After stirring for about 4 hours, the solution was cooled to r.t. diluted with EtOAc, washed with water and brine, and then dried (Na2SO4), filtered and concentrated. Purification by silica gel chromatography (35 g SiO2, 10 to 30% EtOAc/hexanes, over 45 minutes at 35 mL/min) afforded about 418 mg (1.25 mmol, 62%) of N-Boc-4-(2-isobutoxy-phenyl)-piperazine as a colorless oil. LRMS (ESI+): 335.1 [M+1].

Workup

  1. stirringAfter stirring overnight at 60° C.
  2. stirringAfter stirring for about 4 hours
  3. temperaturethe solution was cooled to r.t.
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (35 g SiO2, 10 to 30% EtOAc/hexanes, over 45 minutes at 35 mL/min)

Sources & evidence

ORD record
ord-bca8b1e6f7224e38bcd585a9d2823db1
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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