Triethylamine → HCID 57682613, compound

HRID 1926670Notes

Reaction equation

HRID 1926670 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N: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][CH3:29])=[O:27].C(N(CC)CC)C>C(#N)C.O>[C:1]1([C@@H:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 4368145HCID 4368145, compound

Product 1

HCID 57682613HCID 57682613, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(phenyl(3-(trifluoromethyl)phenyl)methyl)piperazine (2.0 g, 6 mmol) in acetonitrile (20 mL) was added methyl bromoacetate (0.59 mL, 6 mmol) dropwise at rt. The reaction was stirred for 30 min. and triethylamine (3.6 mL, 26 mmol) was added. After stirring for 18 h at rt, the reaction mixture was diluted with water and extracted with CH2Cl2. The organic layers were combined, washed with saturated NaCl solution, then dried over Na2SO4, and concentrated. The crude product was purified by ISCO using 0-40% ethyl acetate or 0-2% ethyl acetate in CH2Cl2 to give a mixture of enantiomers (2.0 g, 80%). The enantiomers were separated by chiral chromatography as described below and two peaks were collected with ˜100% ee.

Workup

  1. stirringAfter stirring for 18 h at rt
  2. extractionextracted with CH2Cl2
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by ISCO
  7. customto give
  8. additiona mixture of enantiomers (2.0 g, 80%)
  9. customThe enantiomers were separated by chiral chromatography
  10. customwere collected with ˜100% ee

Sources & evidence

ORD record
ord-1cb772ac7c3f4dfa801b8248c4c2cb12
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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