Diisopropylamine → HCID 18975666, compound

HRID 2393113Notes

Reaction equation

HRID 2393113 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH:13]1([C:16]#[N:17])[CH2:15][CH2:14]1.[CH:18]1([CH2:23]Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>CCCCCC.O1CCCC1.O.CN1CCCN(C)C1=O>[CH:18]1([CH2:23][C:13]2([C:16]#[N:17])[CH2:15][CH2:14]2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

9

Reactant 4

HCID 7912DiisopropylamineHCID 79637CyclopropanecarbonitrileHCID 12723264(Bromomethyl)cyclopentaneHCID 178418339Butyllithium

Product 1

HCID 18975666HCID 18975666, compoundYield 29.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
0 °C

Procedure

A solution of butyllithium in hexane (2.5M; 80 ml) was added to a solution of diisopropylamine (27.8 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (28.6 ml) in tetrahydrofuran (188 ml) stirring at 0° C. Stirring was continued for 0.5 hours then the mixture was cooled to -78° C. and cyclopropanecarbonitrile (13.4 g) was added. After stirring at -78° C. for a further 1 hour cyclopentylmethylbromide (37.6 g) was added slowly, then the mixture allowed to warm to ambient temperature and stirred for a further 18 hours. The mixture was poured onto water (11) then extracted with ethyl acetate (4×150 ml). The combined extracts were washed with brine then dried over magnesium sulphate and then the solvent was removed in vacuo. Solid material was removed by filtration and the residual oil triturated with ether, solid material again being removed by filtration. The residual oil was then purified by distillation under reduced pressure giving 1-(cyclopentylmethyl)cyclo-propanecarbonitrile (8.9 g) as an oil, bp 50° C./1 mbar.

Workup

  1. stirringStirring
  2. temperaturethe mixture was cooled to -78° C.
  3. additionwas added slowly
  4. temperatureto warm to ambient temperature
  5. stirringstirred for a further 18 hours
  6. extractionthen extracted with ethyl acetate (4×150 ml)
  7. washThe combined extracts were washed with brine
  8. dry with materialthen dried over magnesium sulphate
  9. customthe solvent was removed in vacuo
  10. customSolid material was removed by filtration
  11. customthe residual oil triturated with ether, solid material
  12. customagain being removed by filtration
  13. distillationThe residual oil was then purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-cd1b8b719741467a82186ab08548ae9e
Source dataset
uspto-grants-1998_09
Patent number
US05804586

Reaction notes

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