1-Phenylpiperazine → HCID 670544, compound

HRID 1921315Notes

Reaction equation

HRID 1921315 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][C:14]1[O:18][C:17]([C:19](Cl)=[O:20])=[CH:16][CH:15]=1>ClCCl>[Br:13][C:14]1[O:18][C:17]([C:19]([N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)=[O:20])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 27570115-Bromofuran-2-carbonyl chloride

Product 1

HCID 670544HCID 670544, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Phenylpiperazine (1.3 ml, 8.51 mmol) is added to a mixture of 5-bromofuran-2-carbonyl chloride (1.5 g, 7.16 mmol), piperidinomethylpolystyrene (2.2 g, 3.5 mmol/g, 7.7 mmol) in anhydrous dichloromethane (30 mL) and stirred for 2.5 hr. The reaction mixture is diluted with dichloromethane and filtered through silica gel. The filtrate is concentrated to afford (5-bromo-furan-2-yl)-(4-phenyl-piperazin-1-yl)-methanone as a white solid (1.85 g, 77% yield); MS: m/e=336 (M+H). 1H-NMR (CDCl3, δ ppm) 7.03 (m, 6H); 6.45 (d, 1H); 3.96 (s, 4H); 3.28 (m, 4H).

Workup

  1. filtrationfiltered through silica gel
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-bd03b578bdc34e29b3ab50712db5d2a2
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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