Water → N-[6-(azidomethyl)-1-isoquinolinyl]benzamide

HRID 1279064Notes

Reaction equation

HRID 1279064 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:8][CH:7]=[CH:6]2.C1(P([N:36]=[N+:37]=[N-:38])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.O>C1(C)C=CC=CC=1.O1CCOCC1>[N:36]([CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:8][CH:7]=[CH:6]2)=[N+:37]=[N-:38]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 22665633N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamide

Product 1

HCID 22665816N-[6-(azidomethyl)-1-isoquinolinyl]benzamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To 6.3 g of N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamide (1 g) in 40 mL of toluene and 40 mL of dioxane at 0° C. 7.8 mL of diphenylphosphoryl azide (DDPA) and 5.4 mL of 1,8-diazabicyclo(5.4.0)undec-7ene (DBU) were added. After 24 hours the reaction mixture was poured into water (pH 7) and extracted with ethyl acetate. The organic layer was dried (sodium sulfate) and concentrated. Trituration with diethyl ether gave 6.4 g of the title compound. Mp. 125-129° C. MS (m/e)=303.

Workup

  1. customat 0° C
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0eec1549446046789ce4251ca1a3c85d
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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