Triethylamine → Cyclopentanecarbonyl 4-(methyl)phenyl piperazine

HRID 417995Notes

Reaction equation

HRID 417995 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.CCN(CC)CC.[CH:23]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[CH:23]1([C:28]([CH:11]2[CH2:12][NH:13][CH2:14][CH2:15][N:10]2[C:7]2[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=2)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 831121-(p-Tolyl)piperazine dihydrochloride

Product 1

HCID 66650881Cyclopentanecarbonyl 4-(methyl)phenyl piperazineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylphenyl piperazine dihydrochloride (4.20 g, 16.9 mmol) and NEt3 (7.0 mL, 50.2 mmol) were dissolved in DCM (125 mL) at 0° C. Cyclopentanecarbonyl chloride (2.0 mL, 16.5 mmol) was added and the reaction mixture was allowed to warm to room temperature over 16 hours. The reaction mixture was washed with 1M aq Na2CO3 solution (3×100 mL), dried (MgSO4) and concentrated in vacuo to give cyclopentanecarbonyl 4-(methyl)phenyl piperazine (4.42 g, 98%) as a pale brown oil which was used without further purification.

Workup

  1. washThe reaction mixture was washed with 1M aq Na2CO3 solution (3×100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3297df9f01b645ad96f977418a0a8f14
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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