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Acetic Acid → 1-Butyl-4-[4-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperazine

HRID 32226
Notes
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Reaction equation

HRID 32226 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[C:6]([C:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]([CH3:25])([CH3:24])[CH:17]=2)[CH:5]=1)([O-:3])=[O:2].[CH:26](=O)[CH2:27][CH2:28][CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>O1CCCC1.C(OCC)(=O)C.O>[CH2:26]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[C:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]([CH3:25])([CH3:24])[CH:17]=2)[CH2:11][CH2:12]1)[CH2:27][CH2:28][CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 5049666Sodium triacetoxyborohydrideHCID 231421951-[4-Nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperazine

Product 1

HCID 231416081-Butyl-4-[4-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperazine

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-[4-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperazine (10 mg, 0.029 mmol) produced in Example (88c) in tetrahydrofuran (1 mL) were added butyraldehyde (3.2 mg, 0.044 mmol), sodium triacetoxyborohydride (12 mg, 0.058 mmol) and acetic acid (2 mg, 0.029 mmol) in that order, followed by stirring for 3 hours at room temperature. Water was added to the reaction mixture, extraction was performed with ethyl acetate, and the organic layer was concentrated. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 1-butyl-4-[4-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenyl]piperazine.

Workup

  1. concentrationthe organic layer was concentrated
  2. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-a8dee9b4800f4d7eb96871da9a925981
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425554B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes