Potassium Iodide → 4-[4-(4-Trifluoromethyl-phenyl)-piperazin-1-yl]-butyric acid ethyl ester

HRID 511065Notes

Reaction equation

HRID 511065 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7]Br)[CH3:2].C(N(CC)CC)C.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.[I-].[K+]>O1CCCC1.ClCCl>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][N:28]1[CH2:27][CH2:26][N:25]([C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:31])([F:32])[F:17])=[CH:24][CH:23]=2)[CH2:30][CH2:29]1)[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 76300Ethyl 4-bromobutyrateHCID 1217181-(4-(Trifluoromethyl)phenyl)piperazine

Product 1

HCID 585765934-[4-(4-Trifluoromethyl-phenyl)-piperazin-1-yl]-butyric acid ethyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl-4-bromobutyrate (390 mg, 2.00 mmol) and triethylamine (280 μL; 2.00 mmol) were added to a solution of 1-(4-trifluoromethylphenyl)-piperazine (460 mg; 2.00 mmol) in tetrahydrofuran (3 mL). Potassium iodide (332 mg; 2.00 mmol) was added and the resulting suspension is irradiated in a mono-mode microwave oven for 2 hours at 100° C. The suspension is then diluted with dichloromethane (15 mL) and washed twice with water (5 mL). The organic phase is then dried over sodium sulphate and is concentrated under reduced pressure to afford the desired product (660 mg; 1.96 mmol).

Workup

  1. customthe resulting suspension is irradiated in a mono-mode microwave oven for 2 hours at 100° C
  2. washwashed twice with water (5 mL)
  3. dry with materialThe organic phase is then dried over sodium sulphate
  4. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-3760a034e1e54b5895f97400fcb86c3d
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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