Potassium Carbonate → HCID 58786621, compound

HRID 1376049Notes

Reaction equation

HRID 1376049 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH:16][CH2:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 77432Pentane, 3-(bromomethyl)-HCID 587864641,1-Dimethylethyl 4-[2-amino-1-(2-fluorophenyl)ethyl]-1-piperazinecarboxylate

Product 1

HCID 58786621HCID 58786621, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-[2-Amino-1-(2-fluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (207) (0.18 g, 0.56 mmol) in DMF (3 mL) was added 1-bromo-2-ethyl-butane (0.083 mL, 0.59 mmol) and potassium carbonate (0.093 g, 0.68 mmol). The reaction was allowed to stir at room temperature for 18 h. The reaction mixture was then diluted with EtOAc (30 mL) and H2O (30 mL). The organic phase was dried with sodium sulfate and concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 3% (2M NH3 in MeOH) in MeCl2) yielding 0.13 g (59%) pure product.

Workup

  1. dry with materialThe organic phase was dried with sodium sulfate
  2. concentrationconcentrated to dryness
  3. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 3% (2M NH3 in MeOH) in MeCl2)

Sources & evidence

ORD record
ord-15b9ecfc90c748c5bf50229e2cd70035
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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