Diisopropylethylamine → HCID 86720935, compound

HRID 524878Notes

Reaction equation

HRID 524878 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:11].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:11][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[N:15]1[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 453617314-Bromo-3-chloro-5-nitropyridine

Product 1

HCID 86720935HCID 86720935, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-bromo-3-chloro-5-nitro-pyridine (700 mg, 2.948 mmol), tert-butyl piperazine-1-carboxylate (823.6 mg, 4.422 mmol) and DIPEA (762.0 mg, 1.027 mL, 5.896 mmol) in NMP (2.5 mL) was stirred overnight at RT. The reaction mixture was partitioned between EtOAc and water. Combined organic extract was washed with brine, dried over MgSO4, concentrated under reduced pressure to yield tert-butyl 4-(3-chloro-5-nitropyridin-4-yl)piperazine-1-carboxylate which was used in next step without further purification (1 g, 99%). MS (ES+) 343.1.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. extractionCombined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77189e18eb5c4dd7990e6a0a60a5444d
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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