Dichloromethane → Methanone, (2,4-dibromo-5-thiazolyl)-1-piperidinyl-

HRID 2092968Notes

Reaction equation

HRID 2092968 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([Br:7])[N:6]=1.F[P-](F)(F)(F)(F)F.[N:18]1(OC(N(C)C)=[N+](C)C)[C:22]2C=[CH:24][CH:25]=[CH:26][C:21]=2N=N1.N1CCCCC1.C(Cl)Cl.C(N(CC)CC)C>>[Br:1][C:2]1[S:3][C:4]([C:8]([N:18]2[CH2:24][CH2:25][CH2:26][CH2:21][CH2:22]2)=[O:10])=[C:5]([Br:7])[N:6]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8082PiperidineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 151419582,4-Dibromo-1,3-thiazole-5-carboxylic acid

Product 1

HCID 58227559Methanone, (2,4-dibromo-5-thiazolyl)-1-piperidinyl-Yield 84.7%

Procedure

To a stirred solution of 2,4-dibromo-5-thiazole carboxylic acid (48, 400 mg, 1 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (790 mg, 2.1 mmol) and piperidine (180 uL, 1.8 mmol) in methylene chloride (5.0 mL, 78 mmol) was added triethylamine (580 μL, 4.2 mmol) at room temperature. The resulting turbid mixture was allowed to stir at rt overnight and quenched with water. The product was extracted using dichloromethane and washed with water, citric acid solution, water and brine. Removal of solvent gave the intermediate (49) (2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone (300 mg, 30%) which was used as such for the next step.

Workup

  1. customquenched with water
  2. extractionThe product was extracted
  3. washwashed with water, citric acid solution, water and brine
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-94996aa1c10849c296d338fbfeba324b
Source dataset
uspto-grants-2013_05
Patent number
US08440837B2

Reaction notes

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