Hydrochloric Acid → 2-Methyl-1-(2,3-dimethylphenyl)-3-pyrrolidino-1-propanone hydrochloride

HRID 345500

反応式

HRID 345500 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:12])[CH2:10][CH3:11].[CH2:13]=O.[ClH:15].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.Cl>C(O)(C)C.O>[ClH:15].[CH3:11][CH:10]([CH2:13][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])=[O:12]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 123994421-(2,3-Dimethylphenyl)propan-1-one

生成物 1

HCID 199012002-Methyl-1-(2,3-dimethylphenyl)-3-pyrrolidino-1-propanone hydrochloride収率 64.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

A mixture of 1-(2,3-dimethylphenyl)-1-propanone (11.2 g), paraformaldehyde (2.70 g), pyrrolidine-hydrochloride (9.7g), and hydrochloric acid (0.5 ml) in isopropyl alcohol (15 ml) was refluxed for 8.5 hours. The reaction mixture was evaporated in vacuo to give the residue. The residue was dissolved in water and then washed with ethyl acetate. The aqueous layer was extracted with dichloromethane and then dried over anhydrous magnesium sulfate. The mixture was filtered and then the filtrate was evaporated in vacuo to give the residue. The residue was recrystallized from CH2Cl2 - AcOEt to give 2-methyl-1-(2,3-dimethylphenyl)-3-pyrrolidino-1-propanone hydrochloride (13.1 g, Y: 64.7%) as colorless prisms, m.p. 149°-151° C. IR ν (the free base)maxneat : 1690 cm-1 ##STR323##

後処理

  1. temperaturewas refluxed for 8.5 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customto give the residue
  4. washwashed with ethyl acetate
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customthe filtrate was evaporated in vacuo
  9. customto give the residue
  10. customThe residue was recrystallized from CH2Cl2 - AcOEt

出典と根拠

ORDレコード
ord-c280d2d08684449bb6a22c0779f86dd4
出典データセット
uspto-grants-1991_10
特許番号
US05057535

関連ノート

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