1-Bromo-3-chloropropane → 5-(3-Chloropropyl)octahydrofuro[3,4-c]pyridine

HRID 712502Notes

Reaction equation

HRID 712502 reaction equation
[CH2:1]1[CH:9]2[CH:4]([CH2:5][NH:6][CH2:7][CH2:8]2)[CH2:3][O:2]1.Br[CH2:11][CH2:12][CH2:13][Cl:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:14][CH2:13][CH2:12][CH2:11][N:6]1[CH2:7][CH2:8][CH:9]2[CH2:1][O:2][CH2:3][CH:4]2[CH2:5]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 19825700Octahydrofuro(3,4-c)pyridine

Product 1

HCID 867295055-(3-Chloropropyl)octahydrofuro[3,4-c]pyridineYield 46.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of octahydrofuro[3,4-c]pyridine (300 mg, 2.40 mmol, 1 eq), 1-bromo-3-chloropropane (760 mg, 4.80 mmol, 2 eq) and K2CO3 (736 mg, 9.60 mmol, 4 eq) in acetone (30 mL) was heated to reflux overnight, cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH) to afford the title compound as pale yellow oil (223 mg, 46.5%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 248.05 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-ab942b8225024985bc5b5a48a9eca953
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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