Triethylamine → HCID 58576055, compound

HRID 511142Notes

Reaction equation

HRID 511142 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[N:21]=[C:20]([CH3:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][CH:17]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:16]2[CH:17]=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2531236-Chloro-2-methyl-3-nitropyridineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 58576055HCID 58576055, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (440 mg; 2.2 mmol), 6-chloro-2-methyl-3-nitro-pyridine (346 mg; 2.0 mmol), and triethylamine (420 μL; 3.0 mL) is dissolved in dimethylformamide (6 mL) and the resulting mixture is irradiated in a mono-mode microwave oven for 14 hours at 100° C. The reaction mixture is treated by aq. sat. ammonium chloride (5 mL), the precipitate formed is filtered, then rinsed with water (2 mL) and dried under high vacuum to afford the desired product (590 mg; 1.75 mmol).

Workup

  1. customthe resulting mixture is irradiated in a mono-mode microwave oven for 14 hours at 100° C
  2. customthe precipitate formed
  3. filtrationis filtered
  4. washrinsed with water (2 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-5184ef27dd53421c89b4f8c0d279583b
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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