1-Bromo-3-chloropropane → HCID 86729509, compound

HRID 712507Notes

Reaction equation

HRID 712507 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[C:5]([CH3:12])=[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:11]2[N:3]([CH3:2])[N:4]=[C:5]([CH3:12])[C:6]=2[CH2:7]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 86729508HCID 86729508, compound

Product 1

HCID 86729509HCID 86729509, compoundYield 51.02%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 1,3-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine hydrochloride (2.00 g, 13.22 mmol, 1.0 eq) and K2CO3 (5.47 g, 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) at room temperature. 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 (1.50 g, 51.02%). 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-59929ff7e1964d6cb6fd2f5b2eba6e6b
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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