1-Chloro-3-phenoxy-2-propanol → 7-[3-(3-Phenoxy-2-hydroxypropylamino)-propyl]-theophylline

HRID 614326Notes

Reaction equation

HRID 614326 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:13](=[O:15])[N:11]([CH3:12])[C:10](=[O:16])[N:9]([CH3:17])[C:8]=2[N:7]=[CH:6]1.Cl[CH2:19][CH:20]([OH:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[O:22]([CH2:21][CH:20]([OH:29])[CH2:19][NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:13](=[O:15])[N:11]([CH3:12])[C:10](=[O:16])[N:9]([CH3:17])[C:8]=2[N:7]=[CH:6]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 943001-Chloro-3-phenoxy-2-propanolHCID 29652267-(3-aminopropyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 213292787-[3-(3-Phenoxy-2-hydroxypropylamino)-propyl]-theophylline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 75 g of 7-(3-aminopropyl)-theophylline and 27.4 g of 1-chloro-3-phenoxy-2-propanol is heated for 8 hours at 130° to 140° C. After the melt has been cooled to 70°-90° C., ethanol is added to it, followed by brief boiling under reflux. After standing overnight, the untreated and precipitated aminopropyl theophylline hydrochloride is filtered off under suction, the filtrate is acidified with alcoholic hydrochloric acid, heavily concentrated and acetone added until crystallisation begins. The reaction product then separates and is recrystallised from methanol. Yield 30.2 g. Melting point of the hydrochloride: 183°-186° C.

Workup

  1. temperatureis heated for 8 hours at 130° to 140° C
  2. temperatureAfter the melt has been cooled to 70°-90° C.
  3. temperatureunder reflux
  4. customthe untreated and precipitated aminopropyl theophylline hydrochloride
  5. filtrationis filtered off under suction
  6. concentrationheavily concentrated
  7. additionacetone added until crystallisation
  8. customis recrystallised from methanol
  9. custom183°-186° C.

Sources & evidence

ORD record
ord-efeded0832d9465981883351326e06bc
Source dataset
uspto-grants-1979_03
Patent number
US04144340

Reaction notes

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