1-Bromo-3-chloropropane → HCID 86729489, compound

HRID 712449Notes

Reaction equation

HRID 712449 reaction equation
[CH3:1][C:2]1[O:3][N:4]=[C:5]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=12.Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Cl:15][CH2:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][C:5]2=[N:4][O:3][C:2]([CH3:1])=[C:6]2[CH2:7]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 82418457HCID 82418457, compound

Product 1

HCID 86729489HCID 86729489, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-methyl-4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine (1.60 g), 1-bromo-3-chloropropane (3.50 mL) and cesium carbonate in acetone was heated to reflux for 24 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH) to give the title compound as yellow oil (0.97 g, 39.00%), HPLC: 85.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 215.2 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-4758bf8a36de47a8956feefd523d0d8e
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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