Hydrochloric Acid → 1-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclopentanecarbonitrile

HRID 2260406Notes

Reaction equation

HRID 2260406 reaction equation
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH:13]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.CN1CCN(C)[C:22]1=[O:27].Cl.[CH3:29][CH2:30][CH2:31][CH2:32]CC>O.O1CCCC1>[OH:27][CH2:22][CH2:11][C:10]1[CH:29]=[CH:30][C:31]([CH2:32][C:13]2([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:8][CH:9]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7912DiisopropylamineHCID 8058HexaneHCID 77935CyclopentanecarbonitrileHCID 178418339Butyllithium

Product 1

HCID 189996781-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclopentanecarbonitrileYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-60 °C

Procedure

To a mixture of 38.9 ml (278 mmoles) of diisopropylamine and 320 ml of tetrahydrofuran, cooled to -60° C., there is successively poured dropwise 174 ml of a solution of 1.6M of n-butyllithium in hexane to which 50 ml of tetrahydrofuran have been added, a mixture of 24 g (252 mmoles) of cyclopentanecarbonitrile and of 50 ml of tetrahydrofuran, 65 ml of 1,3-dimethylimidazolidinone and finally 73.95 g (257 mmoles) of the compound prepared in example 26a. The temperature is allowed to rise to 20° C. After 16 hours at 20° C. the mixture is refluxed during 13 hours. After cooling 1000 ml water are added and the mixture is stirred one hour at room temperature before adding 35 ml concentrated HCl and stirring again one hour. The mixture is extracted with ethyl acetate and is thereafter washed with water, dried over Na2SO4, before being concentrated under reduced pressure. The purification is carried out by distillation which gives 41.1 g (yield=71.1%) of a yellow oil. b.p.0.3 =175°-85° C.

Workup

  1. additionhave been added
  2. customto rise to 20° C
  3. temperatureAfter 16 hours at 20° C. the mixture is refluxed during 13 hours
  4. additionare added
  5. stirringstirring again one hour
  6. extractionThe mixture is extracted with ethyl acetate
  7. washis thereafter washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationbefore being concentrated under reduced pressure
  10. customThe purification
  11. distillationis carried out by distillation which

Sources & evidence

ORD record
ord-f5c4257491e34316afc8f186b356935f
Source dataset
uspto-grants-1995_12
Patent number
US05476846

Reaction notes

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