Dichloromethane → HCID 58619015, compound

HRID 1795029Notes

Reaction equation

HRID 1795029 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:21])[CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.[CH2:22](Br)[CH:23]=[CH2:24].C(=O)([O-])[O-].[K+].[K+].ClCCl>CC(C)=O.CO>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C@H:13]([OH:21])[CH2:14][N:15]3[CH2:16][CH2:17][N:18]([CH2:24][CH:23]=[CH2:22])[CH2:19][CH2:20]3)=[CH:7][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Product 1

HCID 58619015HCID 58619015, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

To a solution of (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazin-1-yl-propan-2-ol (300 mg, 1.0 mmol) in acetone (10 ml) was added allyl bromide (0.130 ml, 1.5 mmol) and potasium carbonate (280 mg, 2.0 mmol). The solution was heated to reflux and stirred for 5 hours. Thin layer chromatography (10:1 dichloromethane:methanol) showed formation of product. The solution was cooled and filtered. The filtrate was concentrated under reduced pressure, and the residue purified by preparative chromatography (10:1 dichloromethane:methanol) to yield (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-(4-prop-2-enylpiperazinyl)propan-2-ol (150 mg, M+1=348.2)

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified by preparative chromatography (10:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-9411a18a7d20404d987f19dd19b9cdac
Source dataset
uspto-grants-2006_04
Patent number
US07026321B2

Reaction notes

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