8-(2-Chloroethyl)-8-azaspiro[4.5]decane-7,9-dione → 8-{2-[4-(5-Fluoro-2-methoxyphenyl)piperidin-1-yl]ethyl}-8-azaspiro[4.5]decane-7,9-dione

HRID 49026Notes

Reaction equation

HRID 49026 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.Cl[CH2:17][CH2:18][N:19]1[C:28](=[O:29])[CH2:27][C:22]2([CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:21][C:20]1=[O:30]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:17][CH2:18][N:19]3[C:20](=[O:30])[CH2:21][C:22]4([CH2:26][CH2:25][CH2:24][CH2:23]4)[CH2:27][C:28]3=[O:29])[CH2:10][CH2:9]2)[CH:7]=1

Participants

3

Reactant 2

HCID 114816128-(2-Chloroethyl)-8-azaspiro[4.5]decane-7,9-dioneHCID 155128224-(5-Fluoro-2-methoxyphenyl)piperidine

Product 1

HCID 206351808-{2-[4-(5-Fluoro-2-methoxyphenyl)piperidin-1-yl]ethyl}-8-azaspiro[4.5]decane-7,9-dioneYield 7.5%

Conditions

Temperature
165 °C

Procedure

A mixture of 4-(5-fluoro-2-methoxyphenyl)piperidine (20 mg, 0.096 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 (2.6 mg, 0.0065 mmol, 7%): ESI-MS m/z 403 (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-b8fbb3ff611b4e05b3bc5382864fefd6
Source dataset
uspto-grants-2004_03
Patent number
US06706716B2

Reaction notes

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