Piperidine → HCID 58266651, compound

HRID 1505927Notes

Reaction equation

HRID 1505927 reaction equation
[Br:1][C:2]1[S:6][N:5]=[C:4]([CH2:7]Br)[CH:3]=1.C(N(CC)CC)C.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[Br:1][C:2]1[S:6][N:5]=[C:4]([CH2:7][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 21698464Isothiazole, 5-bromo-3-(bromomethyl)-

Product 1

HCID 58266651HCID 58266651, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-3-bromomethylisothiazole (1.92 g, 7.5 mmol), triethylamine (1.57 mL, 11.2 mmol) and piperidine (1.5 mL, 15.0 mmol) in DCM (10 mL) were stirred for 16 h at ambient temperature. The reaction mixture was partitioned between water (50 mL) and ethyl acetate (75 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a colourless oil (1.49 g, 97%) that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz): 7.25 (s, 1H), 3.59 (s, 2H), 2.46-2.33 (m, 4H), 1.62-1.53 (m, 4H), 1.48-1.38 (m, 2H).

Workup

  1. customThe reaction mixture was partitioned between water (50 mL) and ethyl acetate (75 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0a3117ba41164c609469242eb75ecb29
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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