Hydrochloric Acid → Pirbuterol hydrochloride

HRID 437395Notes

Reaction equation

HRID 437395 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-698ce46ad0944fa2883190a1369c92ab
Source dataset
uspto-grants-1977_06
Patent number
US04031108

Reaction notes

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