Water → 9-Benzyl-9,10-diazatricyclo[4.2.1.12,5]decane

HRID 1912336Notes

Reaction equation

HRID 1912336 reaction equation
[N:1]([CH:4]1[CH2:11][CH2:10][CH:9](Br)[CH:8]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:5]1[CH2:6][CH2:7]2)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH2:14]([N:13]1[CH:5]2[CH2:6][CH2:7][CH:8]1[CH:9]1[NH:1][CH:4]2[CH2:11][CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 508962822-Azido-9-benzyl-5-bromo-9-azabicyclo-[4.2.1]nonane

Product 1

HCID 508962899-Benzyl-9,10-diazatricyclo[4.2.1.12,5]decaneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.44 grams of the azide (1.1A) obtained in Ex. 1.1 are dissolved in 26 ml of anhydrous THF. To this solution 2.96 grams of triphenylphosphine, dissolved in 10 ml of anhydrous THE are added. The mixture is heated at reflux for 5 hours. At the end it is cooled at room temperature and 0.5 ml of water are added. It is further heated at reflux for 14 hours and then cooled at room temperature. The precipitate is filtered under vacuum and washed with THF, suspended in 50 ml of a CH2Cl2/H2O (1/1 v/v) mixture and treated with a 10% by weight K2CO3 aqueous solution up to pH 8. The organic phase is separated, dehydrated with sodium sulphate, filtered and evaporated under vacuum. 2.13 g of 9-benzyl-9,10-diazatricyclo[4.2.1.12,5]decane are recovered. Yield: 91%. 1H-NMR (CDCl3) δ 1.45-1.55 (m, 2H); 1.80-1.90 (m, 4H); 2.00-2.15 (m, 2H); 2.78-2.88 (m, 2H); 3.02-3.12 (m, 2H); 3.31 (s, 2H); 7.20-7.45 (m, 5H). Anal, calc. for C15H20N2: C, 78.90; H, 8.83; N, 12.27. Found: C, 78.71; H, 8.80; N, 12.25.

Workup

  1. additionare added
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 5 hours
  4. temperatureIt is further heated
  5. temperatureat reflux for 14 hours
  6. temperaturecooled at room temperature
  7. filtrationThe precipitate is filtered under vacuum
  8. washwashed with THF
  9. additiontreated with a 10% by weight K2CO3 aqueous solution up to pH 8
  10. customThe organic phase is separated
  11. filtrationfiltered
  12. customevaporated under vacuum
  13. custom2.13 g of 9-benzyl-9,10-diazatricyclo[4.2.1.12,5]decane are recovered

Sources & evidence

ORD record
ord-65d5d741702e4e9cb01f294fc0c7e492
Source dataset
uspto-grants-2013_12
Patent number
US08609659B2

Reaction notes

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