Water → HCID 69523043, compound

HRID 1181434Notes

Reaction equation

HRID 1181434 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[N:7]=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 85869821HCID 85869821, compound

Product 1

HCID 69523043HCID 69523043, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-azidoethyl)isoquinoline (Description 112; 5.6 g, 28.3 mmol) in anhydrous tetrahydrofuran (50 ml) was added triphenylphosphine (14.85 g, 56.6 mmol) and water (0.509 ml, 28.3 mmol), and the resulting mixture stirred at room temperature overnight. The mixture was loaded directly onto a Bond-elut SCX cartridge and eluted with methanol until TLC indicated complete elution of triphenylphosphine. The product was then eluted with 2.0M ammonia in methanol. The basic fractions were collected and evaporated to give the title compound (2.7 g, 55%).

Workup

  1. washeluted with methanol until TLC
  2. washelution of triphenylphosphine
  3. washThe product was then eluted with 2.0M ammonia in methanol
  4. customThe basic fractions were collected
  5. customevaporated

Sources & evidence

ORD record
ord-9f7f975b43284c0db902b008f87c22e5
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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