Theophylline → HCID 4611195, compound

HRID 231067Notes

Reaction equation

HRID 231067 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[CH2:14]([N:16]([CH2:19]C)[CH2:17][CH3:18])[CH3:15].N1CCCC1>O1CCCC1>[N:16]1([CH2:19][N:10]2[C:11]3[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=3[N:8]=[CH:9]2)[CH2:17][CH2:18][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 2153TheophyllineHCID 8471TriethylamineHCID 31268Pyrrolidine

Product 1

HCID 4611195HCID 4611195, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Equivalent amounts of theophylline and triethylamine were allowed to equilibrate with 2 equivalents of 37% aqueous H2C=O for a few minutes until a solution was obtained. Then, 2 equivalents of pyrrolidine was added and the mixture was diluted with tetrahydrofuran and allowed to stir at room temperature overnight. The solution was then concentrated in vacuo at <40°. The residue was triturated with ether and the suspension filtered. The residue from the suspension was dried to give the desired 7-(1-pyrrolidinyl)methyltheophylline in 72% yield; mp 105°-108°, lit mp 108° (J. Org. Chem. 24, 562 (1959); NMR, UV and TLC consistent with the desired product.

Workup

  1. waitto equilibrate with 2 equivalents of 37% aqueous H2C=O for a few minutes until a solution
  2. customwas obtained
  3. concentrationThe solution was then concentrated in vacuo at <40°
  4. customThe residue was triturated with ether
  5. filtrationthe suspension filtered
  6. customThe residue from the suspension was dried

Sources & evidence

ORD record
ord-54b1b968d2db4caaa4633b85f0dcb4b5
Source dataset
uspto-grants-1989_07
Patent number
US04845081

Reaction notes

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