1-(2-Methoxyphenyl)piperazine → HCID 9956415, compound

HRID 2297566Notes

Reaction equation

HRID 2297566 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:13]2[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH2:7][O:6]1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:5]2([CH2:4][CH2:3][CH2:2][N:34]3[CH2:33][CH2:32][N:31]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[O:24][CH3:23])[CH2:36][CH2:35]3)[C:13]3[C:8](=[CH:9][C:10]([C:14]#[N:15])=[CH:11][CH:12]=3)[CH2:7][O:6]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 18382430HCID 18382430, compound

Product 1

HCID 9956415HCID 9956415, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1-(3-chloropropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (2.5 g, 7.9 mmol), 1-(2-methoxyphenyl)piperazine (2.0 g, 10.4 mmol), potassium carbonate (3 g, 22 mmol) and methyl isobutyl ketone (200 mL) was boiled under reflux for 16 h. After cooling to room temperature the organic phase was washed with water (200 mL), the solvents were evaporated in vacuo and the remaining oil purified by column chromatography (ethyl acetate/heptane/triethylamine 75:20:5). The title compound crystallised from diethyl ether 1.5 g (40 %): mp 147-49° C.; 1H NMR (DMSO-d6) δ 1.30-1.65 (m, 2H), 2.10-2.30 (m, 2H), 2.40 (t, 2H), 2.50-2.70 (m, 4H), 2.90-3.20 (m, 4H), 3.85 (s, 3H), 5.20 (m, 2H), 6.70-7.10 (m, 6H), 7.30-7.55 (m, 4H), 7.60 (d, 1H); MS m/z, 472 (MH+, 100), 262 (14), 109 (19).

Workup

  1. temperatureunder reflux for 16 h
  2. washwas washed with water (200 mL)
  3. customthe solvents were evaporated in vacuo
  4. customthe remaining oil purified by column chromatography (ethyl acetate/heptane/triethylamine 75:20:5)
  5. customThe title compound crystallised from diethyl ether 1.5 g (40 %)

Sources & evidence

ORD record
ord-f92b48171d8f46c0bc7805791961e3d2
Source dataset
uspto-grants-2002_12
Patent number
US06492374B2

Reaction notes

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