Sodium Azide → HCID 22048296, compound

HRID 1833263Notes

Reaction equation

HRID 1833263 reaction equation
[CH:1]([O:5][C:6]1[CH:7]=[C:8]([CH:26]=[CH:27][CH:28]=1)[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:24]Cl)=[CH:12][N:11]=1)([CH2:3][CH3:4])[CH3:2].[N-:29]=[N+:30]=[N-:31].[Na+]>CS(C)=O.C(OCC)(=O)C>[N:29]([CH2:24][C:13]1[C:14]2[C:19](=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:10]([CH2:9][C:8]2[CH:26]=[CH:27][CH:28]=[C:6]([O:5][CH:1]([CH2:3][CH3:4])[CH3:2])[CH:7]=2)=[N:11][CH:12]=1)=[N+:30]=[N-:31]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 22048335HCID 22048335, compound

Product 1

HCID 22048296HCID 22048296, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1-(3-sec-butoxy-benzyl)-4-chloromethyl-6,7-dimethoxy-isoquinoline (1.0 g, 2.5 mmol) in dimethylsulfoxide (2 mL) was added to a solution of sodium azide (813 mg, 12.5 mmol) in dimethylsulfoxide (10 mL) prewarmed to 65° C. The solution was stirred at 65° C. for 1½ hrs. The reaction mixture was cooled and dissolved in ethyl acetate (100 mL). This ethyl acetate solution was washed with saturated aqueous sodium bicarbonate solution (2×20 mL), saturated aqueous sodium chloride solution (20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford 4-azidomethyl-1-(3-sec-butoxy-benzyl)-6,7-dimethoxy-isoquinoline (550 mg, 54%) as a light yellow solid which was used without further purification: APCI-MS m/e calcd for C23H26N4O3 (M+H+) 407.5, found 406.9; 1H NMR (300 MHz) compatible.

Workup

  1. customprewarmed to 65° C
  2. temperatureThe reaction mixture was cooled
  3. washThis ethyl acetate solution was washed with saturated aqueous sodium bicarbonate solution (2×20 mL), saturated aqueous sodium chloride solution (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c65d2d47be3e4faca710be3589aaa913
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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