Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]([N:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1)([CH3:11])[CH3:10].[OH-].[K+].C(O)C1C=CC=CC=1>CCOCC>[CH:9]([NH:12][CH2:13][CH:14]([OH:16])[CH2:15][O:8][C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)([CH3:11])[CH3:10]Participants
6
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 6.1 g of 6-methyl-3-pyridinol, 5.5 g of 1-isopropyl-3-azetidinol, 0.3 g of potassium hydroxide and 25 ml of benzyl alcohol is stirred for 16 hours under nitrogen in a bath at 150° C. After cooling, the reaction mixture is diluted with 50 ml of ether and extracted with 30 ml of 4 N hydrochloric acid. The aqueous phase is separated off, rendered alkaline with concentrated sodium hydroxide solution and extracted with 100 ml of methylene chloride. 3-(3'-Isopropylamino-2'-hydroxy-propoxy)-6-methyl-pyridine is isolated from the crude product thus obtained by bulb tube distillation at 130°-140° C. bath temperature and 0.04 mm Hg. It is identical in its properties with the product obtained in Example 19.
Workup
- temperatureAfter cooling
- extractionextracted with 30 ml of 4 N hydrochloric acid
- customThe aqueous phase is separated off
- extractionextracted with 100 ml of methylene chloride
Sources & evidence
- ORD record
- ord-648e995c10494033a116e7bda05572b5
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04410530
Linked notes
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