Benzoyl chloride → n-[[4-[[(2-Pyridinylmethyl)amino]methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydro-8-quinolinyl)-benzamide

HRID 351183Notes

Reaction equation

HRID 351183 reaction equation
[N+](C1C=CC=CC=1S([N:13]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[CH:17][CH:16]=1)(=O)=O)([O-])=O.C(N(CC)CC)C.[C:47](Cl)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[N:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)[C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22018658N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 22256389n-[[4-[[(2-Pyridinylmethyl)amino]methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydro-8-quinolinyl)-benzamideYield 118.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a pre-cooled (ice bath) solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (201 mg, 0.37 mmol) and triethylamine (80 μl, 0.55 mmol) in anhydrous CH2Cl2 (4 mL) was added a solution of benzoylchloride (54 μl, 0.46 mmol) in anhydrous CH2Cl2 (0.5 mL) and the reaction mixture was allowed to stir at room temperature for 18 hours and then concentrated. The residue was diluted with ethylacetate (300 mL), washed with sat. aqueous NaHCO3 then brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2) to give the desired amide (203 mg, 85%) as a yellow oil.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with ethylacetate (300 mL)
  3. washwashed with sat. aqueous NaHCO3
  4. dry with materialbrine, dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-797727f2344f4e31903f00544bee8a3d
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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