tert-Butanol → HCID 18933663, compound

HRID 1598305Notes

Reaction equation

HRID 1598305 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]([CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[CH2:20][N:21]([CH3:23])[CH3:22])[CH3:8])=[CH:4][CH:3]=1.C([OH:30])(C)(C)C.[OH-].[K+]>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:30])=[CH:14][C:13]=2[CH2:20][N:21]([CH3:22])[CH3:23])[CH3:8])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 18933579HCID 18933579, compound

Product 1

HCID 18933663HCID 18933663, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-{2-[N-(4-chlorobenzyl)-N-methylamino]ethoxy}-3-(dimethylaminomethyl)benzonitrile (5.0 g), tert-butanol (50 ml) and powdered potassium hydroxide (10.0 g) was boiled under reflux for 1 hour. The mixture was cooled to ambient temperature and poured into saturated brine (100 ml). The mixture was extracted with dichloromethane to give an oil which solidified slowly on drying under vacuum. The solid obtained was recrystallised from propan-2-ol to give 4-{2-[N-(4-chlorobenzyl)-N-methylamino]ethoxy}-3-(dimethylaminomethyl)benzamide, m.p. 123°-124° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionThe mixture was extracted with dichloromethane
  3. customto give an oil which
  4. customon drying under vacuum
  5. customThe solid obtained
  6. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-efb63e799bd24beab2b3dea249889733
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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