1-(3,4-Difluorophenyl)piperazine → 8-{2-[4-(3,4-Difluorophenyl)piperazin-1-yl]ethyl}-8-azaspiro[4.5]decane-7,9-dione

HRID 49029Notes

Reaction equation

HRID 49029 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].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:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([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])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 27831221-(3,4-Difluorophenyl)piperazineHCID 114816128-(2-Chloroethyl)-8-azaspiro[4.5]decane-7,9-dione

Product 1

HCID 98652548-{2-[4-(3,4-Difluorophenyl)piperazin-1-yl]ethyl}-8-azaspiro[4.5]decane-7,9-dioneYield 40.2%

Conditions

Temperature
165 °C

Procedure

A mixture of 1-(3,4-difluorophenyl)piperazine (21.5 mg, 0.109 mmol) and 8-(2-chloroethyl)-8-azaspiro[4.5]decane-7,9-dione(20 mg, 0.087 mmol) was heated with stirring at 165° C. for 1 hour. 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 (13.7 mg, 0.035 mmol, 40%): 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-e3accd28538d41f4a2ac17b3f2cf071c
Source dataset
uspto-grants-2004_03
Patent number
US06706716B2

Reaction notes

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