1-Bromo-3-chloropropane → HCID 86729496, compound

HRID 712478Notes

Reaction equation

HRID 712478 reaction equation
[O:1]1[CH:10]2[CH:5]([NH:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:12][CH2:13][CH2:14][Cl:15].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:15][CH2:14][CH2:13][CH2:12][N:6]1[CH2:7][CH2:8][CH2:9][CH:10]2[O:1][CH2:2][CH2:3][CH2:4][CH:5]12

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 68842904HCID 68842904, compound

Product 1

HCID 86729496HCID 86729496, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of octahydro-2H-pyrano[3,2-b]pyridine (0.50 g), 1-bromo-3-chloropropane (0.90 mL) and K2CO3 (0.70 g) in acetone was heated to reflux for 10 h, then cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 25:1 (v/v) DCM/MeOH) to give the title compound as yellow oil (0.23 g, 30.00%), HPLC: 80.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 218.5 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 25:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-35ce05ea82fa4e6987028575784c8ee9
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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