Water → 4-[2-(2-Fluorophenoxy)ethyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1928545

Reaction equation

HRID 1928545 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23861061-(2-Bromoethoxy)-2-fluorobenzene

Product 1

HCID 672988034-[2-(2-Fluorophenoxy)ethyl]piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of piperazine-1-carboxylic acid tert-butyl ester (2.79 g, 15 mmol) and 1-(2-bromoethoxy)-2-fluoro-benzene (3.28 g, 15 mmol) in DMF (6 mL) was added cesium carbonate (Cs2CO3, 9.75 g, 30 mmol). The mixture was stirred at room temperature for a day and then treated with water. The aqueous solution was extracted with ethyl acetate and the extract was washed with water and brine. The organic layer was concentrated and the residue was dried under the vacuum to yield the title compound quantitatively as an oil (5.1 g). 1H NMR (400 MHz, DMSO-d6): δ 1.39 (s, 9H), 2.44 (t, 4H), 2.73 (t, 2H), 3.29 (t, 4H), 4.45 (t, 2H), 6.93 (m, 1H), 7.11 (t, 1H), 7.18 (m, 2H).

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. washthe extract was washed with water and brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was dried under the vacuum

Sources & evidence

ORD record
ord-7d878bb266584c8b8fb8c18cda8af50d
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Linked notes

Loading…