1-(2,6-Difluorophenyl)piperazine → 8-{2-[4-(2,6-Difluorophenyl)piperazino]ethyl}-8-azaspiro[4.5]decane-7,9-dione

HRID 49028Notes

Reaction equation

HRID 49028 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[CH2:16][CH2:17][N:18]1[C:27](=[O:28])[CH2:26][C:21]2([CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:20][C:19]1=[O:29]>>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][N:18]2[C:19](=[O:29])[CH2:20][C:21]3([CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:26][C:27]2=[O:28])[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 109324131-(2,6-Difluorophenyl)piperazineHCID 114816128-(2-Chloroethyl)-8-azaspiro[4.5]decane-7,9-dione

Product 1

HCID 98434398-{2-[4-(2,6-Difluorophenyl)piperazino]ethyl}-8-azaspiro[4.5]decane-7,9-dioneYield 26.4%

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2,6-difluorophenyl)piperazine (23.8 mg, 0.120 mmol) and 8-(2-chloroethyl)-8-azaspiro[4.5]decane-7,9-dione(20 mg, 0.087 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 (8.9 mg, 0.023 mmol, 26%): ESI-MS m/z 392 (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-d694fc7536824b37b01b0924c30a4508
Source dataset
uspto-grants-2004_03
Patent number
US06706716B2

Reaction notes

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