Pirbuterol → HCID 13340165, compound

HRID 1632831Notes

Reaction equation

HRID 1632831 reaction equation
N(CC)CC.CC([NH:10][CH2:11][CH:12]([OH:22])[C:13]1[CH:14]=[CH:15][C:16]([OH:21])=[C:17]([CH2:19][OH:20])[N:18]=1)(C)C>CO>[OH:20][CH2:19][C:17]1[C:16]([OH:21])=[CH:15][CH:14]=[C:13]([CH:12]([OH:22])[CH2:11][NH2:10])[N:18]=1

Participants

4

Reactant 2

HCID 4845PirbuterolHCID 8021Diethylamine

Product 1

HCID 13340165HCID 13340165, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 g., (0.005 mole) of 2-acetoxymethyl-3-acetoxy-6-(1-acetoxy-2-N-acetyl-tert-butylaminoethyl)pyridine in 50 ml. of methanol containing 1 ml. of concentrated hydrochloric acid was heated to reflux for 12 hours. The solvents were removed in vacuo and the residue recrystallized from ethyl acetate to give pirbuterol hydrochloride (900 mg., 58%) m.p. 172°-175° C. (dec.), NMR and tlc in 6:3:1 EtOAz:CH3OH:Et2NH identical to pirbuterol. Prolonged heating results in the formation of 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-aminoethyl)pyridine, m.p. 184°-186° dec.

Workup

  1. temperatureProlonged heating

Sources & evidence

ORD record
ord-8f18ca5985d948a384412e967a942935
Source dataset
uspto-grants-1984_10
Patent number
US04477671

Reaction notes

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