1-Bromo-3-chloropropane → HCID 86729512, compound

HRID 712510Notes

Reaction equation

HRID 712510 reaction equation
Cl.[CH3:2][N:3]1[C:11]([CH3:12])=[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]2=[N:4]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CC(C)=O>[Cl:23][CH2:22][CH2:21][CH2:20][N:8]1[CH2:9][CH2:10][C:5]2=[N:4][N:3]([CH3:2])[C:11]([CH3:12])=[C:6]2[CH2:7]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 86729510HCID 86729510, compound

Product 1

HCID 86729512HCID 86729512, compoundYield 44.21%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2,3-dimethyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine hydrochloride (2.0 g, 13.22 mmol, 1.0 eq) and K2CO3 (5.47, 39.66 mmol, 3.0 eq) in 40 mL of acetone was added 1-bromo-3-chloropropane (4.16 g, 26.44 mmol, 2.0 eq). The reaction mixture was heated to reflux for 5.0 h and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (eluting agent: 100:1 (v/v) DCM/MeOH) to give the title compound as yellow oil (1.3 g, 44.21%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 228.73 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5.0 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (eluting agent: 100:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-8ab6e02e12b1406ba7390611ae3865e1
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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