1-(2,4,5-Trifluorophenyl)piperazine → 8-{(1S)-2-[4-(2,4,5-Trifluorophenyl) piperazin-1-yl]-1-methylethyl}-8-azaspiro[4.5]decane-7,9-dione

HRID 49025Notes

Reaction equation

HRID 49025 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:20]1[C:29](=[O:30])[CH2:28][C:23]2([CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:22][C:21]1=[O:31])[CH3:19]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N:10]1[CH2:11][CH2:12][N:13]([CH2:19][C@@H:18]([N:20]2[C:29](=[O:30])[CH2:28][C:23]3([CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:22][C:21]2=[O:31])[CH3:17])[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 113218821-(2,4,5-Trifluorophenyl)piperazineHCID 11470572(S)-8-(2-chloro-1-methylethyl)-8-azaspiro[4.5]decane-7,9-dione

Product 1

HCID 113047778-{(1S)-2-[4-(2,4,5-Trifluorophenyl) piperazin-1-yl]-1-methylethyl}-8-azaspiro[4.5]decane-7,9-dioneYield 52.4%

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2,4,5-trifluorophenyl)piperazine (20 mg, 0.093 mmol) and (S)-8-(2-chloro-1-methylethyl)-8-azaspiro[4.5]decane-7,9-dione (20 mg, 0.082 mmol) was heated with stirring at 160° C. for 5 hours. The residue was purified by preparative HPLC (see Example 8 for conditions), giving (after removal of the solvent) the title compound as a pale yellow oil (18.1 mg, 0.043 mmol, 52%): ESI-MS m/z 424 (MH+).

Workup

  1. temperaturewas heated
  2. customThe residue was purified by preparative HPLC (see Example 8 for conditions)
  3. customgiving (

Sources & evidence

ORD record
ord-15120ed5abbf4ea7981df60e6419f080
Source dataset
uspto-grants-2004_03
Patent number
US06706716B2

Reaction notes

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