Water → [3-(Butylamino)phenyl]methanol

HRID 902236

Reaction equation

HRID 902236 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-ede483588b7f43ec914b02a6faa03a8e
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Linked notes

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