Hydrochloric Acid → HCID 23044175, compound

HRID 1762570Notes

Reaction equation

HRID 1762570 reaction equation
CSC.B.[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:13]=[C:12]([CH2:14][C:15]#[N:16])[C:11]=2[CH:17]=1.Cl.[OH-].[Na+]>O1CCCC1>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:13]=[C:12]([CH2:14][CH2:15][NH2:16])[C:11]=2[CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 23044209HCID 23044209, compound

Product 1

HCID 23044175HCID 23044175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.3 ml (43 mmol) of borane dimethyl sulphide (10M in tetrahydrofuran) are slowly added dropwise, at room temperature, to 5 g (29 mmol) of 2-(5-methoxybenzocyclobuten-1-yl)acetonitrile in 50 ml of tetrahydrofuran. The mixture is then heated under reflux for 30 minutes. Subsequently, while cooling well, 30 ml of 6N hydrochloric acid are added and the mixture is then heated under reflux for a further 30 minutes. The reaction mixture is cooled, adjusted to pH 10 with 4N sodium hydroxide solution and extracted with dichloromethane. The organic phases are combined, dried over sodium sulphate and concentrated under reduced pressure. 2-(5-methoxybenzocyclobuten-1-yl)ethylamine is obtained in the form of a viscous oil; Rf=0.1, toluene/ethanol/conc. aqueous ammonia (90:20:1).

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureSubsequently, while cooling well
  4. temperaturethe mixture is then heated
  5. temperatureunder reflux for a further 30 minutes
  6. temperatureThe reaction mixture is cooled
  7. extractionextracted with dichloromethane
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bbd21226a54749f290a612f3eb6c7d99
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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