Ethyl Bromide → HCID 58780640, compound

HRID 1376037Notes

Reaction equation

HRID 1376037 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[Cl:23])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:30](Br)[CH3:31].[CH3:33][CH2:34]OC(C)=O>CN(C=O)C>[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[Cl:23])[CH2:15][N:16]([CH2:30][CH3:31])[CH2:33][CH3:34])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58780687HCID 58780687, compound

Product 1

HCID 58780640HCID 58780640, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4[-2-Amino-1-(2-chloro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (201) (2.15 g, 6.34 mmol) in DMF (15 mL) was added K2CO3 (4.38 g , 31.71 mmol) and ethyl bromide (2.07 g, 19.03 mmol). The reaction mixture was allowed to stir at room temperature for 18 h. The reaction mixture was diluted with EtOAc (100 mL) and washed with H2O (100 mL) The organic phase was concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 5% MeOH in CHC13) yielding 1.55 g (62%) pure product.

Workup

  1. washwashed with H2O (100 mL) The organic phase
  2. concentrationwas concentrated to dryness
  3. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 5% MeOH in CHC13)

Sources & evidence

ORD record
ord-d66439c127d842549a976b5011c23008
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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