Triethylamine → HCID 70202763, compound

HRID 342598Notes

Reaction equation

HRID 342598 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[F:22][C:23]([F:39])([F:38])[CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(N(CC)CC)C>CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1>[CH2:1]([O:8][CH2:9][C:10]([CH3:15])([CH3:14])[C:11]([N:35]1[CH2:34][CH2:33][N:32]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[O:25][CH2:24][C:23]([F:38])([F:22])[F:39])[CH2:37][CH2:36]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 104915651-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazineHCID 134782883-(Benzyloxy)-2,2-dimethylpropanoic acid

Product 1

HCID 70202763HCID 70202763, compoundYield 85,333.297%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent2×HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-benzyloxy-2,2-dimethylpropionic acid (1.6 g, 7.5 mmol), benzene (10 mL) and DMF (2 drops) was cooled to between 0° and 5° C. and then oxalyl chloride (0.98 mL, 11.2 mmol) was added slowly. The mixture was stirred 1.5 hours at between 20° and 25° C. and concentrated. The residue was dissolved in benzene (10 mL) and the solution reconcentrated (repeated once). The residue then was dissolved in benzene (6 mL) and the solution was cooled to 0° C. and added to a cold (0° C.) mixture of 1-[2-(2,2,2-trifluoroethoxy)phenyl]piperazine (2.1 g, 8.24 mmol) and benzene (6 mL). The mixture was cooled 15 hours at 0° C. and then triethylamine (3 mL, 21.3 mmol) was added. The mixture was stirred an additional 20 minutes, diluted with 10 mL of saturated sodium carbonate and extracted with methylene chloride (3×15 mL). The combined extracts were washed with water (1×10 mL), dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (8:2) to give 3-benzyloxy-2,2-dimethyl-1-{4-[2-(2,2,2-trif-luoroethoxy)phenyl]piperazin-1-yl}-1-propanone (2.8 g, 6.4 mol).

Workup

  1. temperaturewas cooled to between 0° and 5° C.
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in benzene (10 mL)
  4. dissolutionThe residue then was dissolved in benzene (6 mL)
  5. temperatureThe mixture was cooled 15 hours at 0° C.
  6. stirringThe mixture was stirred an additional 20 minutes
  7. extractionextracted with methylene chloride (3×15 mL)
  8. washThe combined extracts were washed with water (1×10 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (8:2)

Sources & evidence

ORD record
ord-af480521526f448f8436b7ae2f68af3b
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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