Chloride → 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one

HRID 855590Notes

Reaction equation

HRID 855590 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1.[NH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1.[Cl-].C(N(C(C)C)CC)(C)C>C(O)C>[OH:1][C@@H:2]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1)[CH2:3][N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 312ChlorideHCID 337214-PiperidoneHCID 81531DiisopropylethylamineHCID 210236065-(((R)-oxiran-2-yl)methoxy)-2-methylbenzo[d]thiazole

Product 1

HCID 587143351-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[((2R)oxiran-2-yl)methoxy]-2-methylbenzothiazole (2.0 g, 9.25 mmol) and piperidin-4-one, chloride (1.25 g, 9.25 mmol) in ethanol was added diisopropylethylamine (1.6 ml, 9.0 mmol). The mixture was heated to reflux for 16 hours. The solvent was removed and the residue purified by column chromatography (10:1 DCM:MeOH) followed by preparative TLC (10:1 DCM:MeOH) to yield 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent was removed
  4. customthe residue purified by column chromatography (10:1 DCM:MeOH)

Sources & evidence

ORD record
ord-e5f9aaad2de54bae8c52ee3958dbafba
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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