Hydrochloric Acid → HCID 89704762, compound

HRID 1051970Notes

Reaction equation

HRID 1051970 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([CH2:14][NH2:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90239225HCID 90239225, compound

Product 1

HCID 89704762HCID 89704762, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A soln. of 1-(6-chloropyridin-3-yl)cyclohexanecarbonitrile (20.1 mmol) in THF (88 mL) was added dropwised to a solution BH3 in THF (60.2 mmol, 1 M). After heating to reflux for 1 h, the reaction mixture was cooled in an ice bath before aq. 2 M HCl (120 mL) was slowly added. The mixture was then heated to reflux for another 20 min. After cooling to RT, the mixture was washed with DCM, then, it was basified with aq. 1 M NaOH and extracted with DCM. The comb. org. layers were dried over MgSO4 and conc. in vacuo.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 1 h
  3. additionwas slowly added
  4. temperatureThe mixture was then heated
  5. temperatureto reflux for another 20 min
  6. washthe mixture was washed with DCM
  7. extractionextracted with DCM
  8. dry with materiallayers were dried over MgSO4 and conc. in vacuo

Sources & evidence

ORD record
ord-e99af59ebe5e48e1b5f5e0a16ef789de
Source dataset
uspto-grants-2016_07
Patent number
US09388198B2

Reaction notes

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