1-(2,4,5-Trifluorophenyl)piperazine → 8-{(1R)-1-Phenyl-2-[4-(2,4,5-trifluorophenyl)piperazino]ethyl}-8-azaspiro[4.5]decane-7,9-dione

HRID 49030Notes

Reaction equation

HRID 49030 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl[CH2:17][C@H:18]([N:25]1[C:34](=[O:35])[CH2:33][C:28]2([CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:27][C:26]1=[O:36])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:19]1([C@@H:18]([N:25]2[C:34](=[O:35])[CH2:33][C:28]3([CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:27][C:26]2=[O:36])[CH2:17][N:13]2[CH2:12][CH2:11][N:10]([C:3]3[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=3[F:1])[CH2:15][CH2:14]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 113218821-(2,4,5-Trifluorophenyl)piperazineHCID 69886549(R)-8-(2-chloro-1-phenylethyl)-8-azaspiro[4.5]decane-7,9-dione

Product 1

HCID 99350858-{(1R)-1-Phenyl-2-[4-(2,4,5-trifluorophenyl)piperazino]ethyl}-8-azaspiro[4.5]decane-7,9-dioneYield 30.3%

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2,4,5-trifluorophenyl)piperazine (20 mg, 0.093 mmol) and (R)-8-(2-chloro-1-phenylethyl)-8-azaspiro[4.5]decane-7,9-dione (20 mg, 0.066 mmol) was heated with stirring at 160° C. for 5 hours. The residue was purified by preparative TLC, giving the title compound as an off-white solid (9.5 mg, 0.020 mmol, 30%): ESI-MS m/z 486 (MH+).

Workup

  1. temperaturewas heated
  2. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-a5d6b001e83f41bba4b5b2fcb59b14cf
Source dataset
uspto-grants-2004_03
Patent number
US06706716B2

Reaction notes

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