Water → 1-(4-n-Octyloxyphenyl)-4-tert-butoxycarbonylpiperazine

HRID 1872356Notes

Reaction equation

HRID 1872356 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O>CN(C)C=O.C(OCC)(=O)C>[CH2:27]([O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 116877404-(4-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 211824491-(4-n-Octyloxyphenyl)-4-tert-butoxycarbonylpiperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 1-(4-Hydroxyphenyl)-4-tert-butoxycarbonylpiperazine (3 g) and potassium carbonate (0.82 g) in N,N-dimethylformamide (15 ml) was added octyl bromide (1.87 ml). The mixture was stirred for 10 hours at 70° C. The reaction mixture was added to a mixture of water and ethyl acetate. The organic layer was taken, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel, and eluted with (hexane : ethyl acetate=9:1). The fractions containing the object compound were combined, and evaporated under reduced pressure to give 1-(4-n-Octyloxyphenyl)-4-tert-butoxycarbonylpiperazine (2.71 g).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationThe magnesium sulfate was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. washeluted with (hexane : ethyl acetate=9:1)
  5. additionThe fractions containing the object compound
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ea45349c290b44c88997654852ac3161
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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