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

HRID 2304289Notes

Reaction equation

HRID 2304289 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 (1g) 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-4d74c3330aaf4d2da80fa9d762909b6b
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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