Triethylamine → HCID 69486552, compound

HRID 1071396Notes

Reaction equation

HRID 1071396 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.[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1.[CH2:33](N(CC)CC)C>ClCCl>[Cl:23][C:24]1([CH3:33])[CH:32]=[CH:31][C:27]([C:28]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]3[CH:19]=[CH:20][C:21]([Cl:22])=[C:2]([Cl:1])[CH:3]=3)[CH2:11][CH2:10]2)=[O:29])=[CH:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 11325154HCID 11325154, compound

Product 1

HCID 69486552HCID 69486552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-chlorobenzoyl chloride (60 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 49.6 mg of the product, which was subsequently repurified by silica gel chromatography to afford 11.4 mg product: MS m/z 473 (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 49.6 mg of the product, which
  6. customwas subsequently repurified by silica gel chromatography

Sources & evidence

ORD record
ord-cba1c08a04e44f25b1d76839fd70881d
Source dataset
uspto-grants-2005_06
Patent number
US06906073B2

Reaction notes

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