Triethylamine → HCID 68537407, compound

HRID 1993642Notes

Reaction equation

HRID 1993642 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.Cl.[CH3:13][C:14]([CH3:24])([CH3:23])[C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:13][C:14]([CH3:24])([CH3:23])[C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=2)[CH2:19][CH2:18]1)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3453642-Chloro-4-methyl-5-nitropyridineHCID 68540093HCID 68540093, compound

Product 1

HCID 68537407HCID 68537407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a solution of 2-chloro-4-methyl-5-nitro-pyridine (0.85 mmol, 0.15 g), 2,2-dimethyl-1-piperazin-1-yl-propan-1-one hydrochloride (0.94 mmol, 0.16 g) and triethylamine (2.12 mmol, 0.3 mL) in a sealed tube at 80° C. overnight. Cool down the mixture to room temperature, add CH2Cl2 and wash with saturated aq. sodium chloride. Dry over sodium sulfate, filter, and concentrate under reduced pressure to give 2,2-dimethyl—[4-(4-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-propane-1-one. Subject residue to silica gel chromatography eluting with hexanes/ethyl acetate in a gradient (from 30% up to 60%). MS(ES): m/z=307 [M+H].

Workup

  1. washwash with saturated aq. sodium chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-d9ba5287425e490fa1bbcccd1b6ca5ac
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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