Water → 1-[4-(3-Hydroxypropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

HRID 376962Notes

Reaction equation

HRID 376962 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[C:9]([N:18]([CH3:20])[CH3:19])([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:10])=[CH:4][CH:3]=1.[NH2:22][CH2:23][CH2:24][CH2:25][OH:26].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[OH:26][CH2:25][CH2:24][CH2:23][NH:22][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[C:9]([N:18]([CH3:20])[CH3:19])([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 187550662-(Dimethylamino)-1-(4-fluorophenyl)-2-methyl-3-phenylpropan-1-one

Product 1

HCID 193606261-[4-(3-Hydroxypropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

10.0 g (0.035 mol) of 1-(4-fluorophenyl)-2-dimethylamino-2-benzyl-propan-1-one and 18.4 g (0.25 mol) of 3-amino-1-propanol are dissolved in 20 ml of dry dimethylacetamide, and the solution is heated up to 150° C. together with 9.7 g (0.07 mol) of potassium carbonate, and stirred overnight (about 12 hours). After the solution is cooled down, it is poured into 300 ml of water and extracted with toluene. The organic phase is washed with water and saturated sodium chloride solution, and dried over MgSO4. After distilling off the toluene, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:1) as an eluent, and an oily product is obtained. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm]:1.14 (s, 3H), 1.50 (br, 1H), 1.93 (m, 2H), 2.33 (s, 6H), 2.96 (d, 1H), 3.37 (m, 2H), 3.42 (d, 1H), 3.85 (m, 2H), 4.45 (br, 1H), 6.56 (d, 2H), 6.89-6.91 (m, 2H), 7.10-7.12 (m, 3H), 8.45 (d, 2H).

Workup

  1. temperatureAfter the solution is cooled down
  2. extractionextracted with toluene
  3. washThe organic phase is washed with water and saturated sodium chloride solution
  4. dry with materialdried over MgSO4
  5. distillationAfter distilling off the toluene
  6. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:1) as an eluent
  7. customan oily product is obtained

Sources & evidence

ORD record
ord-e4270b9bfd6d4d28876be1e60ddaef99
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

Loading…