Water → [3-(Butylamino)phenyl]methanol

HRID 496781

Reaction equation

HRID 496781 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C([O-])(O)=O.[Na+].Br[CH2:16][CH2:17][CH2:18][CH3:19].O>CS(C)=O>[CH2:16]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][OH:6])[CH:3]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 802933-Aminobenzyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 22322603[3-(Butylamino)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3.69 g (30 mmol) of 3-amino benzyl alcohol in 20 ml DMSO was added 3.78 g (45 mmol) solid NaHCO3 and 2.91 ml (27 mmol) 1-bromobutane. The reaction was allowed to stir at 50° C. for 18 hours (overnight). Reaction was worked up by adding 250 ml water and product was extracted in ethyl acetate. Water was added, and the resultant mixture was extracted with EtOAc. The organic layer was washed with water and brine.

Workup

  1. customReaction
  2. extractionwas extracted in ethyl acetate
  3. additionWater was added
  4. extractionthe resultant mixture was extracted with EtOAc
  5. washThe organic layer was washed with water and brine

Sources & evidence

ORD record
ord-09101997df5349ed8a295f2fba2bb391
Source dataset
uspto-grants-2005_09
Patent number
US06946481B1

Linked notes

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