N-(5-Chloro-2-methylphenyl)piperazine → 8-{2-[4-(5-Chloro-2-methylphenyl)piperazino]ethyl}-8-azaspiro[4.5]decane-7,9-dione

HRID 49027Notes

Reaction equation

HRID 49027 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=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]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:16][CH2:17][N:18]3[C:19](=[O:29])[CH2:20][C:21]4([CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:26][C:27]3=[O:28])[CH2:12][CH2:13]2)[CH:7]=1

Participants

3

Reactant 2

HCID 693767N-(5-Chloro-2-methylphenyl)piperazineHCID 114816128-(2-Chloroethyl)-8-azaspiro[4.5]decane-7,9-dione

Product 1

HCID 98874588-{2-[4-(5-Chloro-2-methylphenyl)piperazino]ethyl}-8-azaspiro[4.5]decane-7,9-dioneYield 49.4%

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(5-chloro-2-methylphenyl)piperazine (20 mg, 0.095 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 (17.3 mg, 0.043 mmol, 49%): ESI-MS m/z 404 (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-8ed87a0303924bdb9d401702469b228a
Source dataset
uspto-grants-2004_03
Patent number
US06706716B2

Reaction notes

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