tert-Butanol → HCID 18933639, compound

HRID 1598304Notes

Reaction equation

HRID 1598304 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH3:10])=[C:4]([CH2:22][N:23]([CH3:25])[CH3:24])[CH:3]=1.[OH-].[K+].C([OH:32])(C)(C)C>[Cl-].[Na+].O.C(#N)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:32])=[CH:14][CH:13]=2)[CH3:10])=[C:4]([CH2:22][N:23]([CH3:25])[CH3:24])[CH:3]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 18933646HCID 18933646, compound

Product 1

HCID 18933639HCID 18933639, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-{N-[2-(4-chloro-2-dimethylaminomethylphenoxy) ethyl]-N-[methyl]aminomethyl}benzonitrile (10.16 g), powdered potassium hydroxide (20.0 g) and tert-butanol (100 ml) was boiled under reflux for 30 minutes. The mixture was cooled to ambient temperature and poured into saturated brine (300 ml). The mixture was extracted with dichloromethane to give an oil which was dissolved in hot acetonitrile and cooled to yield a precipitate which was collected by filtration and recrystallised from ethyl acetate/petroleum ether b.p. 60°-80° C., to give 4-{N-[2-(4-chloro-2-dimethylaminomethylphenoxy) ethyl]-N-[methyl]aminomethyl}benzamide, m.p. 108°-109° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. extractionThe mixture was extracted with dichloromethane
  3. customto give an oil which
  4. temperaturecooled
  5. customto yield a precipitate which
  6. filtrationwas collected by filtration
  7. customrecrystallised from ethyl acetate/petroleum ether b.p. 60°-80° C.

Sources & evidence

ORD record
ord-39d37bca1b5a41949e947c66c8a6b32b
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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