1-Bromo-3-chloropropane → N-(3-chloropropyl)-N-methylcyclobutanamine

HRID 273042Notes

Reaction equation

HRID 273042 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][CH2:15][CH2:16][Cl:17]>C(#N)C>[Cl:17][CH2:16][CH2:15][CH2:14][N:2]([CH3:1])[CH:3]1[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 21830191N-Methylcyclobutanamine

Product 1

HCID 68576572N-(3-chloropropyl)-N-methylcyclobutanamineYield 38.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-methylcyclobutanamine (1 g, 3.89 mmol) and potassium carbonate (1.18 g, 8.56 mmol) in acetonitrile (20 ml) at 0° C. was added 1-bromo-3-chloropropane (383 μl, 3.89 mmol). Reaction was warmed to room temperature and stirred for 24 hours. Solid removed by filtration and filtrate concentrated in vacuo to give the title compound (241 mg, 38%) as an oil. No purification was performed. LRMS APCI+ m/z 162 [MH]+.

Workup

  1. customReaction
  2. customSolid removed by filtration and filtrate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cef92e9b6b04a0bbbfdf96f0c023154
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

Loading…