Dimethylformamide → HCID 66751021, compound

HRID 534883Notes

Reaction equation

HRID 534883 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O.Cl.Cl.[C:31]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)([CH3:34])([CH3:33])[CH3:32]>O1CCCC1.O.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:44]2[CH2:45][CH2:46][N:41]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:42][CH2:43]2)=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 738804-(Benzyloxy)benzoic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751021HCID 66751021, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-(benzyloxy)benzoic acid (913 mg) and N,N-dimethylformamide (0.01 mL) in tetrahydrofuran (30 mL) was added oxalyl chloride (0.508 mL) at room temperature. After 1 h the reaction mixture was concentrated under reduced pressure to provide the residue and the residue was dissolved in tetrahydrofuran (30 mL). A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.0 g) and triethylamine (1.67 mL) was added to the solution and stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (NH-silica gel, ethyl acetate) to provide the title compound (1360 mg, 79%) as a solid.

Workup

  1. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  2. customto provide the residue
  3. additionwas added to the solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by flash column chromatography (NH-silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-17fef0cf471840488b87fc7003a24342
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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