Isopropylamine → 1-[(2-Methoxypyridin-3-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

HRID 1764335Notes

Reaction equation

HRID 1764335 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][CH:11]([OH:18])[CH2:12]OS(C)(=O)=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>C(O)(C)C>[CH:19]([NH:22][CH2:12][CH:11]([OH:18])[CH2:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 20483430HCID 20483430, compound

Product 1

HCID 204834691-[(2-Methoxypyridin-3-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

22 g of crude 2-methoxy-3-(3'-methanesulphonyloxy-2'-hydroxy-propoxy)-pyridine, 50 ml of isopropylamine and 150 ml of isopropanol are heated for 16 hours under reflux. After working up analogously to Example 14, 3-(3'-isopropylamino-2'-hydroxypropoxy)-2-methoxy-pyridine is obtained, which melts at 50°-65° C. after recrystallisation from ether-pentane. After reaction with half the equivalent amount of fumaric acid, the neutral fumarate of melting point 146°-147° C. (recrystallised from acetone) is obtained.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-0249530fbdf14aedbf472f0370129631
Source dataset
uspto-grants-1978_09
Patent number
US04115575

Reaction notes

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