Cyclohexanone → HCID 58625059, compound

HRID 390253Notes

Reaction equation

HRID 390253 reaction equation
[CH3:1][O:2][CH:3]([O:21][CH3:22])[C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[O:7][C:8]1[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl>[CH:23]1([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]3[CH:15]=[CH:16][C:17]([N+:18]([O-:20])=[O:19])=[C:4]([CH:3]([O:2][CH3:1])[O:21][CH3:22])[CH:5]=3)[CH:9]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride2×HCID 586250523-(3-Dimethoxymethyl-4-nitro-phenoxy)phenylamine

Product 1

HCID 58625059HCID 58625059, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(3-Dimethoxymethyl-4-nitro-phenoxy)-phenylamine (0.0125 mol) was dissolved in DCE (150 mL), and cyclohexanone (0.0125 mol) was added, followed by NaBH(OAc)3 (0.0187 mol). The reaction mixture was stirred overnight at room temperature. Some extra NaBH(OAc)3 was added, and the reaction mixture was stirred overnight at room temperature. A 10% NaOH solution (150 mL) was added, and this mixture was extracted with diisopropyl ether. The separated organic layer was dried (MgSO4) and filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: 20:80 up to 5:95 hexane:CH2Cl2). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. extractionthis mixture was extracted with diisopropyl ether
  3. dry with materialThe separated organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: 20:80 up to 5:95 hexane:CH2Cl2)
  7. customThe product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8249cb8a45ad4a6786e47322d9db0e85
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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