Sodium Hydroxide → N1-Cyclobutylpropane-1,3-diamine

HRID 1776250Notes

Reaction equation

HRID 1776250 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([NH:11][CH2:12][CH2:13][C:14]#[N:15])[CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.O>[CH:7]1([NH:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 183489093-(Cyclobutylamino)propionitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 61778021N1-Cyclobutylpropane-1,3-diamineYield 66.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a cooled (0° C.) suspension of lithium aluminum hydride (3.056 g, 80.5 mmol) in anhydrous diethyl ether (120 mL) was added a solution of 3-(cyclobutylamino)propanenitrile (5.000 g, 40.3 mmol) in anhydrous diethyl ether (40 mL), dropwise over 45 mins. The reaction mixture was stirred at room temperature for 15 mins and at reflux for 4 hrs, cooled to room temperature and stirred for 1 hr. The mixture was cooled to 0° C. and vigorously stirred while water (3.1 mL) was added dropwise, followed by 15% aqueous sodium hydroxide (3.1 mL), and finally water (9.3 mL). The resultant slurry was warmed to room temperature, stirred for 15 mins, and anhydrous magnesium sulfate added, stirring for an additional 15 mins. Solid materials were removed by filtration, washing multiple times with warm methylene chloride, and the filtrate concentrated under reduced pressure to give the desired product as a pale yellow liquid (3.44 g, 66%). 1H NMR (CDCl3, 300 MHz) 3.14 (m, 1H), 2.69-2.62 (m, 2H), 2.53-2.45 (m, 2H), 2.13-2.10 (m, 2H), 1.56-1.48 (m, 6H), 1.33 (br s, 3H).

Workup

  1. temperatureTo a cooled
  2. temperatureat reflux for 4 hrs
  3. temperaturecooled to room temperature
  4. stirringstirred for 1 hr
  5. temperatureThe mixture was cooled to 0° C.
  6. additionwas added dropwise
  7. temperatureThe resultant slurry was warmed to room temperature
  8. stirringstirred for 15 mins
  9. stirringstirring for an additional 15 mins
  10. customSolid materials were removed by filtration
  11. washwashing multiple times with warm methylene chloride
  12. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff1268a338b2480c8137cb1dfa250451
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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