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Hydroxylamine HCl → 4-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzaldehydeoxime

HRID 32249
Notes
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Reaction equation

HRID 32249 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:20]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[OH:30][NH3+:31].C([O-])(=O)C.[Na+].[Cl-].[NH4+]>C(OCC)(=O)C.O.C(O)C>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[N:31][OH:30])=[CH:13][C:12]=2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:20]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 21645Hydroxylamine HClHCID 25517Ammonium ChlorideHCID 517045Sodium AcetateHCID 231425004-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzaldehyde

Product 1

HCID 740205524-(4-t-Butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzaldehydeoximeYield 105.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the crude product of 4-(4-t-butylcyclohexyl)-3-(4-butylpiperazin-1-yl)benzaldehyde produced in Example (101b) (247 mg), hydroxylammonium chloride (134 mg, 1.93 mmol) and ethanol (10 mL) were added sodium acetate (193 mg, 2.35 mmol) and water (1.5 mL), followed by stirring for 2 hours at room temperature. The reaction mixture was poured into ice water, and then ethyl acetate and saturated aqueous solution of ammonium chloride were added and extraction was performed with ethyl acetate. The separated organic layer was washed with brine and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure to give 271 mg of a crude product of the title compound as a light yellow solid. This product was directly used without purification for the following reaction.

Workup

  1. extractionextraction
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ec9889d94e2147858c604e0aa01348c5
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