Hydrochloric Acid → Pirbuterol hydrochloride

HRID 1604956Notes

Reaction equation

HRID 1604956 reaction equation
[ClH:1].CC1(C)[O:8][C:7]2[CH:9]=[CH:10][C:11]([CH:13]([OH:20])[CH2:14][NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][C:6]=2[CH2:5][O:4]1>CO>[ClH:1].[ClH:1].[OH:4][CH2:5][C:6]1[C:7]([OH:8])=[CH:9][CH:10]=[C:11]([CH:13]([OH:20])[CH2:14][NH:15][C:16]([CH3:18])([CH3:17])[CH3:19])[N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21428405α-[[(1,1-Dimethylethyl)amino]methyl]-2,2-dimethyl-4H-1,3-dioxino[5,4-b]pyridine-6-methanol

Product 1

HCID 68658Pirbuterol hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml. of methanol and 10 ml. of 10% hydrochloric acid is added 227 mg. of 2,2-dimethyl-6-(1-hydroxy-2-t-butylaminoethyl)-4H-pyrido[3,2-d]-1,3-dioxin, and the resulting reaction mixture allowed to stir at room temperature for 1.5 hrs. Removal of the solvents under vacuum at 70° C. provides 230 mg. of the desired product, which is identical by nuclear magnetic resonance spectroscopy to the product in U.S. Pat. No. 3,700,681.

Workup

  1. customRemoval of the solvents under vacuum at 70° C.
  2. customprovides 230 mg

Sources & evidence

ORD record
ord-8ce32a7bcc354aeaabf688ad27b29157
Source dataset
uspto-grants-1976_04
Patent number
US03948919

Reaction notes

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