3,5-Dichlorobenzoic acid → HCID 69677706, compound

HRID 584179Notes

Reaction equation

HRID 584179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=O.Cl.Cl.[CH2:14]([N:21]1[CH2:26][CH2:25][NH:24][C@H:23]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=2)[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl>[CH2:14]([N:21]1[CH2:26][CH2:25][N:24]([C:5](=[O:7])[C:4]2[CH:8]=[C:9]([Cl:11])[CH:10]=[C:2]([Cl:1])[CH:3]=2)[C@H:23]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=2)[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 58113,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 69677639HCID 69677639, compound

Product 1

HCID 69677706HCID 69677706, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3,5-dichlorobenzoic acid (2.6 g), (3R)-1-benzyl-3-(3,4-dimethylbenzyl)piperazine dihydrochloride (5.0 g) and triethylamine (8.54 ml) in dichloromethane (80 ml) was added 2-chloro-1-methylpyridinium iodide (3.83 g) under ice-cooling, and then the mixture was stirred at room temperature for 1 hour. The mixture was evaporated under reduced pressure, and the resulting residue was dissolved into ethyl acetate. The ethyl acetate solution was filtrated and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using hexane-ethyl acetate (10:1) as eluent to give (2R)-4-benzyl-1-(3,5-dichlorobenzoyl)-2-(3,4-dimethylbenzyl)piperazine (5.58 g).

Workup

  1. temperaturecooling
  2. customThe mixture was evaporated under reduced pressure
  3. dissolutionthe resulting residue was dissolved into ethyl acetate
  4. filtrationThe ethyl acetate solution was filtrated
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a9a685f5d03b47ce865147e082efce45
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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