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4-Methoxybenzylamine → 1-(4-Methoxy-benzyl)-4-(4-nitro-phenyl)-piperidine-2,6-dione

HRID 340535
Notes
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Reaction equation

HRID 340535 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][C:14](=[O:16])O[C:12](=[O:17])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>C1COCC1>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:25]2[C:12](=[O:17])[CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:15][C:14]2=[O:16])=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 178879674-(4-Nitrophenyl)oxane-2,6-dione

Product 1

HCID 597711911-(4-Methoxy-benzyl)-4-(4-nitro-phenyl)-piperidine-2,6-dioneYield 669%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 12.6 g (53.6 mmol) of 4-(4-nitro-phenyl)-dihydro-pyran-2,6-dione (as prepared in the previous step) in THF (160 mL) was treated with 9.04 mL (6.96 mmol) of 4-methoxy-benzylamine at RT for 2 h. Solvents were evaporated in vacuo. The residue was dissolved in 1.0 N HCl (200 mL) and extracted with EtOAc (2×250 mL). The combined organic layers were washed with water (1×200 mL), dried (MgSO4) and concentrated in vacuo. The residue was treated with acetic anhydride (200 mL) and triethylamine (30 mL), and heated to 85° C. for 1.5 h. The mixture was concentrated in vacuo, treated with 1.0 N HCl (200 mL), and extracted with EtOAc (3×200 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (1×200 mL) and water (1×200 mL), dried (MgSO4), and concentrated in vacuo. The solid was triturated with hexane using sonication, filtered and air-dried to afford 16.5 g (87%) of the title compound as light tan solid: Mass spectrum (ESI, m/z): Calcd. for C19H21N2O, 325.1 (M—OCH3+2H). found 325.0.

Workup

  1. customSolvents were evaporated in vacuo
  2. dissolutionThe residue was dissolved in 1.0 N HCl (200 mL)
  3. extractionextracted with EtOAc (2×250 mL)
  4. washThe combined organic layers were washed with water (1×200 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with acetic anhydride (200 mL) and triethylamine (30 mL)
  8. concentrationThe mixture was concentrated in vacuo
  9. additiontreated with 1.0 N HCl (200 mL)
  10. extractionextracted with EtOAc (3×200 mL)
  11. washThe combined organic layers were washed with saturated aqueous NaHCO3 (1×200 mL) and water (1×200 mL)
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated in vacuo
  14. customThe solid was triturated with hexane using sonication
  15. filtrationfiltered
  16. customair-dried

Sources & evidence

ORD record
ord-164da5e66f7e4bf2844d9dfadcdd10a1
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895584B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes