Triethylamine → 7-Hexanoyloxymethyl theophylline

HRID 461012Notes

Reaction equation

HRID 461012 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH:9][CH2:10][N:11]1[C:20]2[C:19](=[O:21])[N:17]([CH3:18])[C:16](=[O:22])[N:15]([CH3:23])[C:14]=2[N:13]=[CH:12]1.C(N(CC)CC)C.CCCCCCC.C(Cl)Cl>C(Cl)Cl>[C:1]([O:9][CH2:10][N:11]1[C:20]2[C:19](=[O:21])[N:17]([CH3:18])[C:16](=[O:22])[N:15]([CH3:23])[C:14]=2[N:13]=[CH:12]1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 641347-Hydroxymethyl theophyllineHCID 67340Hexanoyl chlorideHCID 21907733Dichloromethane heptane

Product 1

HCID 234551707-Hexanoyloxymethyl theophyllineYield 43.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.71 g (0.0053 mole) of hexanoyl chloride in 10 ml of CH2Cl2 there was added 1.10 g (0.0052 mole) of 7-hydroxymethyl theophylline; no reaction occurred and the reaction mixture was a suspension. Then 0.58 g (0.0057 mole) of triethylamine was added and a clear, colorless solution was obtained. The solution was stirred at room temperature for 15 minutes then concentrated in vacuo. The residue was titrated with 200 ml ether and filtered. The filtrate was concentrated in vacuo to give an oil which was titrated with heptane CH2Cl2 (50:10). The resulting suspension was filtered while hot and concentrated to 20 ml, then cooled to room temperature. A gelatinous mass precipitated which was filtered and dried to give 0.70 g (mp 67°-72° C, 43% yield) of the desired product.

Workup

  1. customa clear, colorless solution was obtained
  2. concentrationthen concentrated in vacuo
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give an oil which
  6. filtrationThe resulting suspension was filtered while hot and
  7. concentrationconcentrated to 20 ml
  8. temperaturecooled to room temperature
  9. customA gelatinous mass precipitated which
  10. filtrationwas filtered
  11. customdried

Sources & evidence

ORD record
ord-fafaa4ce559646a580a7394a4a269550
Source dataset
uspto-grants-1977_12
Patent number
US04061753

Reaction notes

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