1-Bromo-3-chloropropane → HCID 86729488, compound

HRID 712444Notes

Reaction equation

HRID 712444 reaction equation
[CH2:1]1[NH:5][CH2:4][CH:3]2[CH2:6][O:7][CH2:8][CH2:9][CH:2]12.C([O-])([O-])=O.[K+].[K+].[Cl:16][CH2:17][CH2:18][CH2:19]Br>CC(C)=O>[Cl:16][CH2:17][CH2:18][CH2:19][N:5]1[CH2:1][CH:2]2[CH2:9][CH2:8][O:7][CH2:6][CH:3]2[CH2:4]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 68539279HCID 68539279, compound

Product 1

HCID 86729488HCID 86729488, compoundYield 16.96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of octahydropyrano[3,4-c]pyrrole (0.14 g) in acetone (30 mL) was added K2CO3 (0.76 g) followed by 1-chloro-3-bromopropane (0.57 g, 2.0 eq). The reaction mixture was heated to reflux for 12 h and filtered. The filtrate was concentrated in vacuo, and the residue was dissolved in EtOAc (100 mL). The solution was washed with water (100 mL×2) followed by brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) EA/CH3OH) to give the title compound (38 mg, 16.96%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 204.7 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in EtOAc (100 mL)
  6. washThe solution was washed with water (100 mL×2)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) EA/CH3OH)

Sources & evidence

ORD record
ord-1c6a468933a942dd8bfb914a9cf1c0ad
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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