1-Acetylpiperazine → HCID 9960686, compound

HRID 1795005Notes

Reaction equation

HRID 1795005 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][O:11][C:10]2[N:15]=[C:16](Cl)[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[C:9]=2[C:8]1=[O:27].[C:37]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)(=[O:39])[CH3:38]>O>[C:37]([N:40]1[CH2:45][CH2:44][N:43]([C:16]2[CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[C:9]3[C:8](=[O:27])[N:7]([CH2:6][C:5]4[CH:4]=[C:3]([C:2]([F:36])([F:35])[F:1])[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=4)[CH2:14][CH2:13][CH2:12][O:11][C:10]=3[N:15]=2)[CH2:42][CH2:41]1)(=[O:39])[CH3:38]

Participants

4

Reactant 2

HCID 837951-AcetylpiperazineHCID 22179334HCID 22179334, compound

Product 1

HCID 9960686HCID 9960686, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-7-(2-methylphenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (compound of Reference Example 17; 100 mg) and 1-acetylpiperazine (73.0 mg) was stirred at 150° C. for 5 hours. To the resulting residue, water was added, and then the mixture was subjected to extraction with ethyl acetate. The resulting extract was dried on anhydrous sodium sulfate. The solvent was removed by distillation to obtain a residue, and then the residue was purified on silica gel column chromatography (ethyl acetate: methanol=10:1) to obtain 9-(4-acetylpiperazine-1-yl)-5-[3,5-bis(trifluoromethyl)benzyl]-7-(2-methylphenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (44.6 mg, 38%).

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. extractionThe resulting extract
  3. dry with materialwas dried on anhydrous sodium sulfate
  4. customThe solvent was removed by distillation
  5. customto obtain a residue
  6. customthe residue was purified on silica gel column chromatography (ethyl acetate: methanol=10:1)

Sources & evidence

ORD record
ord-f7fd05ecc50b484fa0f4180bef3787f2
Source dataset
uspto-grants-2006_04
Patent number
US07026309B2

Reaction notes

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