1-(2-Methoxyphenyl)piperazine → (R)-1-(2-Methoxyphenyl)-4-[2-(methyl)-2-(2-pyridinylamino)ethyl]piperazine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH3:15][C@@H:16]1[CH2:20]OS(=O)(=O)[N:17]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([CH3:20])[NH:17][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:11][CH2:10]1Participants
Procedure
12.02 grams of 1-(2-methoxyphenyl)piperazine and 13.4 grams of (R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide were stirred together in 50 millilitres of acetonitrile at room temperature overnight. The solvent was removed in vacuo. The residue was heated in 100 millilitres of dilute hydrochloric acid for 30 minutes. The mixture was cooled, washed with dichloromethane, basified by using dilute sodium hydroxide solution and extracted by means of dichloromethane. The organic phase was washed with water, dried and evaporated to dryness to give 15.8 g of the title compound as a slightly crude product. The product was 85 to 95% pure and contained 2 main impurities derived from the sulphone. The crude product was used directly, i.e. without purification, by acylation by means of cyclohexanecarbonyl chloride to yield (R)-N-[1-methyl-2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl) cyclohexanecarboxamide.
Workup
- customThe solvent was removed in vacuo
- temperatureThe residue was heated in 100 millilitres of dilute hydrochloric acid for 30 minutes
- temperatureThe mixture was cooled
- washwashed with dichloromethane
- extractionextracted by means of dichloromethane
- washThe organic phase was washed with water
- customdried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-57eee1fbc18f461a9ac7d450376aeee5
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06175012B1
Reaction notes
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