Water → HCID 67106795, compound

HRID 1623674Notes

Reaction equation

HRID 1623674 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]([OH:16])=O)=[O:10].CN1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.O>ClCCl.CN(C)C=O>[C:22]1([CH2:21][O:20][C:19]2[CH:18]=[CH:17][C:13]([C:14]([N:32]3[CH2:33][CH2:34][CH2:1][CH2:30][CH2:31]3)=[O:16])=[CH:12][C:11]=2[C:9]([O:8][CH3:7])=[O:10])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 531671-MethylpiperazineHCID 65578Oxalyl chlorideHCID 671067771285516-45-1

Product 1

HCID 67106795HCID 67106795, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.61 ml, 6.99 mmol) was added dropwise to a stirred solution of 3-[(methyloxy)carbonyl]-4-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 49; 400 mg, 1.40 mmol) in dichloromethane (10 ml) and dimethylformamide (3 drops) at room temperature. The mixture was stirred at room temperature for 1 h. The solvent was then removed and the residue was dissolved in dichloromethane (5 ml). This mixture was added to a solution of 1-methylpiperazine (525 mg, 5.24 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 2 h. Water (60 ml) was added to the mixture, which was then extracted with dichloromethane (3×60 ml). The organic phase was washed with saturated brine (50 ml), dried over sodium sulfate and evaporated in vacuo to give the crude product. The crude product was loaded onto a silica gel (200 g) column and eluted with dichloromethane/methanol=50:1 to yield the title compound as a colourless oil. 450 mg.

Workup

  1. customThe solvent was then removed
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. stirringThe mixture was stirred at room temperature for 2 h
  4. extractionwas then extracted with dichloromethane (3×60 ml)
  5. washThe organic phase was washed with saturated brine (50 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto give the crude product
  9. washeluted with dichloromethane/methanol=50:1

Sources & evidence

ORD record
ord-e7f3f9ca94c149c2b8c3c04e87b8cbab
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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