Benzyl piperazine-1-carboxylate → Benzyl 4-(6-((tert-butyldimethylsily)oxy)hexyl)piperazine-1-carboxylate

HRID 1944859Notes

Reaction equation

HRID 1944859 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[N:16]1([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>CC#N>[Si:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:19]1[CH2:18][CH2:17][N:16]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:21][CH2:20]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 643495Benzyl piperazine-1-carboxylateHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilane

Product 1

HCID 58505092Benzyl 4-(6-((tert-butyldimethylsily)oxy)hexyl)piperazine-1-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate 19 (2.6 g, 8.8 mmol) was added to a stirring solution of benzyl piperazine-1-carboxylate (1.1 mL, 5.87 mmol) in CH3CN (80 mL). The reaction mixture was refluxed over night, cooled, and quenched with satd. NaHCO3 (100 mL). The aqueous layer was extracted with EtOAc (3×50 mL) and the combined organic layers were washed with brine, dried over Na2SO4, concentrated to give the crude (3.8 g) as opaque oil. The chromatography (1:3, hexanes/EtOAc) afforded the title compound (1.78 g, 70%) as clear oil. ES/MS calcd. for C24H43N2O3Si+ 435.3. Found m/z=435.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed over night
  2. temperaturecooled
  3. customquenched with satd
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give the crude (3.8 g) as opaque oil

Sources & evidence

ORD record
ord-b7517b6ce9024bc09510a8896555697d
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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