Triethylamine → 96392-15-3

HRID 615865Notes

Reaction equation

HRID 615865 reaction equation
[CH:1]1[N:6]=[C:5](Cl)[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.[NH2:20][CH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1.C(N(CC)CC)C>C(O)C>[CH:21]1([NH:20][C:5]2[C:4]3[N:8]=[CH:9][N:10]([C:3]=3[N:2]=[CH:1][N:6]=2)[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2[OH:19])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 123445(+-)-1-Aminoindan

Product 1

HCID 18069696392-15-3Yield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Four grams 6-Chloropurine riboside, 2.32 g 1-aminoindane and 2.11 g of triethylamine are refluxed in 100 ml of absolute ethanol under nitrogen for 20 hours. Volatiles are evaporated to dryness. Residue is dissolved in 20 ml 2-propanol and diluted with 200 ml H2O. Clear aqueous solution is decanted and residual oily material is washed with cold water. Coevaporation with ethanol several times gives solid material. Crystallization from CHCl3 /2-propanol (10:1) and hexane affords 3.0 g (56.2%) N(6)-(1-indanyl)adenosine having a melting point of 120°-122° C. (foam).

Workup

  1. customVolatiles are evaporated to dryness
  2. dissolutionResidue is dissolved in 20 ml 2-propanol
  3. additiondiluted with 200 ml H2O
  4. customClear aqueous solution is decanted
  5. washresidual oily material is washed with cold water
  6. customCoevaporation with ethanol several times gives solid material
  7. customCrystallization from CHCl3 /2-propanol (10:1) and hexane

Sources & evidence

ORD record
ord-cba93c7a50f743d5b44e68df49fe660f
Source dataset
uspto-grants-1985_02
Patent number
US04501735

Reaction notes

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