Water → HCID 19360612, compound

HRID 376965

Reaction equation

HRID 376965 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[C:9]([N:19]([CH3:21])[CH3:20])([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH3:11])=[CH:4][CH:3]=1.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[OH:27][CH2:26][CH2:25][CH2:24][NH:23][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[C:9]([N:19]([CH3:21])[CH3:20])([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 90863-Amino-1-propanolHCID 11430Potassium CarbonateHCID 193605992-Benzyl-2-(dimethylamino)-1-(4-fluorophenyl)butan-1-one

Product 1

HCID 19360612HCID 19360612, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

15.0 g (0.050 mol) of 1-(4-fluorophenyl)-2-dimethylamino-2-benzyl-butan-1-one and 26.3 g (0.35 mol) of 3-amino-1-propanol are dissolved in 30 ml of dry dimethylacetamide, and the solution is heated up to 150° C. together with 13.8 g (0.1 mol) of potassium carbonate, and stirred overnight (about 12 h). After the solution is cooled down, it is poured into 300 ml of water and extracted with ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution, and dried over MgSO4. After distilling off the ethyl acetate, 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]: 0.68 (t, 3H), 1.52 (br, 1H), 1.82-1.94 (m, 3H), 2.00-2.07 (m, 1H), 2.35 (s, 6H), 3.17 (d, 1H), 3.20 (d, 1H), 3.32-3.37 (m, 2H), 3.81-3.85 (m, 2H), 4.42 (br, 1H), 6.52 (d, 2H), 7.14-7.28 (m, 5H), 8.32 (d, 2H).

Workup

  1. temperatureAfter the solution is cooled down
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and saturated sodium chloride solution
  4. dry with materialdried over MgSO4
  5. distillationAfter distilling off the ethyl acetate
  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-3ce85f544e7544c6bee7c395f9f17ae8
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Linked notes

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