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Ethyl Acetate → 4-(3-Chloro-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1993638
Notes
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Reaction equation

HRID 1993638 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 685401434-(3-Chloro-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Place 2,3-dichloro-5-nitro-pyridine (2.0 g, 10.36 mmol), piperazine-1-carboxylic acid tert-butyl ester (2.12 g, 11.40 mmol), and potassium carbonate (1.72 g, 12.43 mmol) in DMF (20 mL). Heat to 80° C. for 2.5 days. Cool to room temperature and add ethyl acetate and water. Separate organic layer and wash with water and saturated aq. sodium chloride. Collect organic layer, dry over Mg2SO4, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography eluting with 20% EtOAc:hexane to yield 3.29 g (93%) of 4-(3-chloro-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester. MS(ES): m/z=341 [M+H].

Workup

  1. temperatureCool to room temperature
  2. washSeparate organic layer and wash with water and saturated aq. sodium chloride
  3. dry with materialCollect organic layer, dry over Mg2SO4
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. washSubject residue to silica gel chromatography eluting with 20% EtOAc

Sources & evidence

ORD record
ord-ddb6dec00f7f4fdab871ea617e4a4de5
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07652015B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes