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Acetone → 1-Boc-4-isopropylpiperazine

HRID 58191
Notes
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Reaction equation

HRID 58191 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1CCN([C:22]2[CH:23]=CC([N+]([O-])=O)=C(N)[CH:27]=2)CC1)C.CC(C)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O.C(O)(=O)C.C(Cl)Cl>[CH:22]([N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]1)([CH3:23])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 180AcetoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 598459045-(4-Ethylpiperazin-1-yl)-2-nitroaniline

Product 1

HCID 105613521-Boc-4-isopropylpiperazine

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

Boc piperizine, 1 (10 g, 53.76 mmol) and acetone (4 mL) was taken in a mixture of dry DCM (100 mL) and acetic acid (3.2 mL). Stirred at room temperature for 20 min. Added Na(OAc)3BH (17 g, 80.2 mmol) and stirring continued at room temperature for 12 hr. The reaction mixture was diluted with water, extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to get crude title compound (13 g, crude). MS (ESI): 229.2 [M+H]+.

Workup

  1. waitcontinued at room temperature for 12 hr
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8cdb9919f49d4d87862b635031fe59b5
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434697B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes