Diisopropylethylamine → HCID 60441266, compound

HRID 1868014Notes

Reaction equation

HRID 1868014 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:15]2[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 60441266HCID 60441266, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-butyl piperazine-1-carboxylate (3.0 g, 16.11 mmol) and 2-chloro-3-trifluoromethyl pyridine (2.93 g, 16.11 mmol) charged to a microwave vial was added with diisopropylethylamine (7.05 mL, 40.28 mmol) and DMF (1.0 mL). The reaction mixture was subject to microwave irradiation at 160° C. for 30 minutes. The reaction mixture was partitioned between EtOAc and water, organic layer washed with brine and dried over Na2SO4. The crude product obtained by solvent evaporation was purified via flash column chromatography. 4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester was obtained in 33.9% yield (1.81 g) as light yellow oil.

Workup

  1. customirradiation at 160° C. for 30 minutes
  2. customThe reaction mixture was partitioned between EtOAc and water, organic layer
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product obtained by solvent evaporation
  6. customwas purified via flash column chromatography

Sources & evidence

ORD record
ord-ab94050dc3084f98bbd8022cf1ba0c13
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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