Ammonium Acetate → HCID 58071456, compound

HRID 1256014Notes

Reaction equation

HRID 1256014 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][C:15](=O)[C:14]([CH3:20])([CH3:19])[CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([NH2:27])[C:14]([CH3:20])([CH3:19])[CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 580714961-(3-Methoxy-4-nitrophenyl)-3,3-dimethylpiperidin-4-one2×

Product 1

HCID 58071456HCID 58071456, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1-(3-Methoxy-4-nitrophenyl)-3,3-dimethylpiperidin-4-one (INTERMEDIATE 39) (278 mg, 1 mmol) and ammonium acetate (771 mg, 10.0 mmol) in MeOH (5 mL) was stirred at RT overnight. Sodium cyanoborohydride (75 mg, 1.2 mmol) were added. The reaction was stirred at RT for 2 h. MeOH (20 mL) and silica gel (5 g) was added. The mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel (5% MeOH and 1% NH4OH in CH2Cl2) to give the title product (0.2 g, 72.0%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel (5% MeOH and 1% NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-5650e9c7abb34a31854d3c342274c7ab
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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