Ethyl bromoacetate → HCID 58494006, compound

HRID 1942705Notes

Reaction equation

HRID 1942705 reaction equation
[Br:1][C:2]1[C:3]([CH2:15][CH3:16])=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH2:15][CH3:16])=[C:4]([CH:8]=[C:9]2[CH2:10][CH2:11][N:12]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 58494028HCID 58494028, compound

Product 1

HCID 58494006HCID 58494006, compoundYield 111.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[(3-bromo-2-ethylphenyl)methylidene]piperidine (D137) (0.53 g, 1.891 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added potassium carbonate (3.92 g, 28.4 mmol), followed by ethyl bromoacetate (0.190 mL, 1.702 mmol). The reaction solution was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate, washed with water, dried over sodium sulphate, concentrated to afford ethyl {4-[(3-bromo-2-ethylphenyl)methylidene]-1-piperidinyl}acetate (D142) (0.693 g). MS (ES): C18H24BrNO2 requires 365.1. found 366.1 (M+H+).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-40cc0d54454e4a5ab5d2b2e44bce5e41
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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