Ethyl bromoacetate → HCID 68735485, compound

HRID 2382184Notes

Reaction equation

HRID 2382184 reaction equation
[C:1]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(N(CC)CC)C>CC#N.O>[C:1]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 68733876HCID 68733876, compound

Product 1

HCID 68735485HCID 68735485, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To solution of N-phenyl-N-(3-(trifluoromethyl)phenyl)piperidin-4-amine (1.3 g, 4.1 mmol) in MeCN (15 mL) was added ethyl bromoacetate (0.50 ml, 4.5 mmol) followed by triethylamine (1.1 ml, 8.1 mmol). The reaction mixture was stirred at RT for 4 h, diluted with water and extracted with DCM. The combined DCM layer was dried (Na2SO4), and concentrated. The product was purified with ISCO using 0-15% EtOAc in DCM to give ethyl 2-(4-(phenyl(3-(trifluoromethyl)phenyl)amino)piperidin-1-yl)acetate (1.2 g, 73% yield).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined DCM layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe product was purified with ISCO

Sources & evidence

ORD record
ord-214871f427b2423c88dc0dd10ae397a8
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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