Triethylamine → (+)-(3,5-Dimethylbenzoyl)-3-(3,4-dichlorophenyl)piperazine

HRID 362538Notes

Reaction equation

HRID 362538 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][NH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[C:19](O)=[O:20].O.ON1C2C=CC=CC=2N=N1.CCN(CC)CC>C(Cl)Cl>[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[C:19]([N:13]1[CH2:12][CH2:11][NH:10][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:14]1)=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 103563,5-Dimethylbenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 42313562-(3,4-Dichlorophenyl)piperazine

Product 1

HCID 10292159(+)-(3,5-Dimethylbenzoyl)-3-(3,4-dichlorophenyl)piperazineYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of CH2Cl2 (600 mL) containing 2-(3,4-dichlorophenyl)piperazine (6.934 g, 30 mmol), 3,5-dimethylbenzoic acid (4.55 g, 30 mmol), and N-hydroxybenzotriazole monohydrate (4.05 g, 30 mmol) at -20° C. were added Et3N (4.2 mL, 30 mmol) and N,N-dimethylaminopropylethylcarbodimide (DEC) (5.86 g, 30 mmol) under nitrogen. The reaction was kept at -20° C. for an hour and gradually warmed to RT overnight. After stirring 22 hours, the reaction was complete and CH2Cl2 (200 mL) was added. The organic solution was washed with brine (150 mL, 3×), dried over MgSO4 , filtered and concentrated under vacuum to give 8.2 g of crude product. The product was crystallized from CH2Cl2 /Hexane to give a light yellow solid (6.3 g, 17.34 mmol, 57.8%), m.p.139°-141° C.; FAB MS [M+1]+ 35 Cl 363.1.

Workup

  1. waitThe reaction was kept at -20° C. for an hour
  2. washThe organic solution was washed with brine (150 mL, 3×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give 8.2 g of crude product
  7. customThe product was crystallized from CH2Cl2 /Hexane

Sources & evidence

ORD record
ord-e9ebd2f29c474f09a017160676750579
Source dataset
uspto-grants-1999_02
Patent number
US05869488

Reaction notes

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