Water → HCID 86695321, compound

HRID 572834Notes

Reaction equation

HRID 572834 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]([O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)[C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:11]=[CH:12][CH:13]=1.[N-:32]=[N+:33]=[N-:34].[Na+].O>CS(C)=O>[N:32]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]([O:24][CH:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)[C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:11]=[CH:12][CH:13]=1)=[N+:33]=[N-:34]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 66835890HCID 66835890, compound

Product 1

HCID 86695321HCID 86695321, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-[[3-(5-chloropentyloxy)phenyl](1-methyl-piperidin-4-yloxy)-methyl]benzothiazole (200 mg) and sodium azide (85 mg) in dimethylsulfoxide (3 mL) is heated overnight at 70° C., then cooled back to room temperature. Water is added and the product is extracted with ethyl acetate. Pooled extracts are washed with water, then brine, dried over magnesium sulfate and concentrated under reduced pressure to give 2-[[3-(5-azidopentyloxy)phenyl](1-methyl-piperidin-4-yloxy)methyl]benzothiazole used without further purification.

Workup

  1. temperaturecooled back to room temperature
  2. extractionthe product is extracted with ethyl acetate
  3. washPooled extracts are washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72da8b14a7d94ae187045f2536e87fe9
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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