(3-Methoxyphenyl)acetic acid → HCID 21241497, compound

HRID 1761452Notes

Reaction equation

HRID 1761452 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([N:29]2[CH2:30][CH2:31][N:26]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:27][CH2:28]2)=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 15719(3-Methoxyphenyl)acetic acidHCID 65578Oxalyl chlorideHCID 759941-BenzylpiperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 21241497HCID 21241497, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

3-Methoxyphenylacetic acid (100 g, 600 mmole) was dissolved in methylene chloride (600 mL) and treated with oxalyl chloride (60 mL) and DMF (1 mL) at room temperature. The mixture was stirred for four hours until gas evolution ceased. The solvent was evaporated and the residue dried under vacuum to remove excess oxalyl chloride. The oil obtained was dissolved in methylene chloride (400 mL). Half of this solution (200 mL, approx. 300 mmole) was cooled in ice and treated with a solution of 1-benzylpiperazine (60 mL, 350 mmole) and triethylamine (30 mL) in methylene chloride (100 mL) dropwise. The mixture was stirred at room temperature for 16 hours. Sodium bicarbonate solution was added and the mixture stirred for 15 minutes. The layers were separated. The organic phase was washed with water, brine, dried over K2CO3 and evaporated to an oil. Wt. 90 g. A small portion was characterized as the hydrochloride, m.p. 229°-231° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue dried under vacuum
  3. customto remove excess oxalyl chloride
  4. customThe oil obtained
  5. stirringThe mixture was stirred at room temperature for 16 hours
  6. stirringthe mixture stirred for 15 minutes
  7. customThe layers were separated
  8. washThe organic phase was washed with water, brine
  9. dry with materialdried over K2CO3
  10. customevaporated to an oil

Sources & evidence

ORD record
ord-fbeaac927f67448c94ae0a4d19c0f742
Source dataset
uspto-grants-1989_05
Patent number
US04826844

Reaction notes

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