Hydrochloric Acid → 3-(Dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one

HRID 1096693

反応式

HRID 1096693 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:12])[CH2:10][CH3:11])[CH:6]=[CH:7][CH:8]=1.Cl.[CH3:14][NH:15][CH3:16].[CH2:17]=O.Cl.[OH-].[Na+]>CC(O)C.O.C1(C)C=CC=CC=1>[CH3:14][N:15]([CH3:16])[CH2:11][CH:10]([CH3:17])[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:12]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 5847653'-Methoxypropiophenone

生成物 1

HCID 193604953-(Dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 3776Isopropanol溶媒

実験手順

A mixture of 1-(3-methoxyphenyl)-1-propanone (240 g) in 2-propanol (584 ml) is stirred at ambient temperature. Dimethylamine hydrochloride (238.3 g) is added, followed by paraformaldehyde (109.5 g) and an aqueous HCl solution (26.5 ml, 35% w/w). The reaction mixture is heated to reflux temperature and stirred and refluxed for 5 hours. The reaction mixture is allowed to cool to 20° C., and water (730 ml) and toluene (146 ml) are added. The upper organic layer is discarded and an aqueous NaOH solution (50% w/w, 175.2 ml) is added to the water layer while stirring for 10 minutes and keeping the temperature below 25° C. After 10 minutes the layers are allowed to separate, the upper organic layer is isolated and washed with water (219 ml). The organic layer is isolated and concentrated to obtain 3-(dimethylamino)-1-(3-methoxyphenyl)-2-methyl-1-propanone as on oily residue (294.9 g).

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux temperature
  3. stirringstirred
  4. temperaturerefluxed for 5 hours
  5. temperatureto cool to 20° C.
  6. stirringwhile stirring for 10 minutes
  7. customthe temperature below 25° C
  8. customto separate
  9. customthe upper organic layer is isolated
  10. washwashed with water (219 ml)
  11. customThe organic layer is isolated
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d349ac241e14194854d073a5b487246
出典データセット
uspto-grants-2012_03
特許番号
US08138376B2

関連ノート

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