Acetone → 1-[(3-Methylpyridin-2-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

HRID 647980Notes

Reaction equation

HRID 647980 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([OH:14])[CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][N:8]=1.C([BH3-])#N.[Na+].[CH3:19][C:20]([CH3:22])=O>CO>[OH:14][CH:4]([CH2:3][NH:2][CH:20]([CH3:22])[CH3:19])[CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 204835331-Amino-3-[(3-methylpyridin-2-yl)oxy]propan-2-ol

Product 1

HCID 204835171-[(3-Methylpyridin-2-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4 ml of a 2 N solution of hydrogen chloride in methanol are added to a solution of 3.6 g of 2-(3'-amino-2'-hydroxy-propoxy)-3-methyl-pyridine and 1.5 g of sodium cyanoborohydride in 70 ml of methanol and 12 ml of acetone are added dropwise over the course of approx. 30 minutes, whilst stirring. The reaction mixture is stirred overnight at room temperature and is then evaporated in vacuo and the residue is acidified with 2 N hydrochloric acid. The aqueous solution is extracted once by shaking with 30 ml of ether. The hydrochloric acid phase is separated off and rendered alkaline with concentrated sodium hydroxide solution. 2-(2'-Hydroxy-3'-isopropylamino-propoxy)-3-methyl-pyridine is isolated by extraction with ethyl acetate and is identical with the material described in Example 21.

Workup

  1. additionare added dropwise over the course of approx. 30 minutes
  2. stirringThe reaction mixture is stirred overnight at room temperature
  3. customis then evaporated in vacuo
  4. extractionThe aqueous solution is extracted once
  5. stirringby shaking with 30 ml of ether
  6. customThe hydrochloric acid phase is separated off

Sources & evidence

ORD record
ord-63e5f333eae64bbbaf72137874d4965e
Source dataset
uspto-grants-1983_10
Patent number
US04410530

Reaction notes

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