Dimethylformamide → HCID 22458192, compound

HRID 2184849Notes

Reaction equation

HRID 2184849 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Br[CH2:19][CH2:20][OH:21].CCN(C(C)C)C(C)C.CN(C=O)C>O>[OH:21][CH2:20][CH2:19][N:13]1[CH2:14][CH2:15][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][C:2]([F:1])([F:16])[F:17])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 81531DiisopropylethylamineHCID 107529251-(2-Trifluoromethoxyphenyl)piperazine

Product 1

HCID 22458192HCID 22458192, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 1.23 g of 1-(2-trifluoromethoxyphenyl)piperazine, 0.73 mL of 97% 2-bromoethanol, 1.25 mL of DIPEA and 4 mL of DMF was heated at 65° C. for 6 h. After cooling to r.t., the mixture was diluted with H2O (50 mL) and extracted with CH2Cl2 (3×30 mL). The organic layer was dried (anhydrous Na2SO4) and evaporated to dryness in vacuo. The residue was purified by flash chromatography (CH2Cl2-MeOH 100:1.5) affording 0.911 g (63%) of the title compound.

Workup

  1. temperatureAfter cooling to r.t.
  2. extractionextracted with CH2Cl2 (3×30 mL)
  3. dry with materialThe organic layer was dried (anhydrous Na2SO4)
  4. customevaporated to dryness in vacuo
  5. customThe residue was purified by flash chromatography (CH2Cl2-MeOH 100:1.5)

Sources & evidence

ORD record
ord-c95f844559df41358d24c5cb20c8eb2d
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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