Propargyl bromide → 1-(Prop-2-yn-1-yl)piperidine

HRID 1676252Notes

Reaction equation

HRID 1676252 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:14][C:15]#[CH:16]>CC(C)=O>[CH2:16]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:15]#[CH:14]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8082PiperidineHCID 10796Cesium carbonate

Product 1

HCID 3366521-(Prop-2-yn-1-yl)piperidineYield 56.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Prepared using methodology as described in US 2005/0026944. To a stirred mixture of piperidine (851 mg, 10.0 mmol), cesium carbonate (3.26 g, 10.0 mmol) and acetone (20 mL) was added 3-bromoprop-1-yne (1.49 g, 10.0 mmol; 80% in toluene) at room temperature. The white suspension was stirred for 18 hours at room temperature. The suspension was filtered, and the filtrate was concentrated. The resulting residue was triturated with diethyl ether (10 mL), filtered, and the filtrate concentrated to obtain the product as an oil (0.70 g, 56%). 1H NMR (400 MHz, CDCl3) δ 3.27 (d, J=2 Hz, 2H), 2.50 (m, 4H), 2.22 (t, J=2 Hz, 1H), 1.62 (m, J=6 Hz, 4H), 1.43 (m, 2H).

Workup

  1. customPrepared
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was triturated with diethyl ether (10 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0e124b48d32041258bc6ba86ecf33cf4
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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