Piperidine → HCID 58266651, compound

HRID 1888464Notes

Reaction equation

HRID 1888464 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-5e608b9b926c4200b2756671ed0c2f10
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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