4-Methylbenzoyl Chloride → HCID 10217040, compound

HRID 1071397Notes

Reaction equation

HRID 1071397 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:8][CH2:7]1.[CH3:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(N(CC)CC)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][C:24]([CH3:23])=[CH:25][CH:26]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 11325154HCID 11325154, compound

Product 1

HCID 10217040HCID 10217040, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-[4-(3,4-dichlorobenzyl)-piperazin-1-yl]-phenylamine (45 mg) was dissolved in a solution of triethylamine in dichloromethane (3 mL, 0.29 M in triethylamine). This solution was added to a test tube containing 4-methylbenzoyl chloride (55 mg). After standing at ambient temperature for several days, the reaction was directly passed through a small pad of silica and eluted with 10% ethyl acetate in hexanes, then with 50% ethyl acetate in hexanes. Solvent removal left 10.7 mg of the product: MS m/z 453 (M)+.

Workup

  1. additionThis solution was added to a test tube
  2. waitAfter standing at ambient temperature for several days
  3. washeluted with 10% ethyl acetate in hexanes
  4. customSolvent removal
  5. waitleft 10.7 mg of the product

Sources & evidence

ORD record
ord-448e50a9cfcb4c8fb65026579707e247
Source dataset
uspto-grants-2005_06
Patent number
US06906073B2

Reaction notes

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