Acetic Acid → [2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amine

HRID 1828968

反応式

HRID 1828968 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](=O)[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:15]([NH2:17])[CH3:16].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:17][CH2:15][CH3:16])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 698962-Propanone, 1-(3,4-dimethoxyphenyl)-HCID 5003444Sodium cyanoborohydride

生成物 1

HCID 22061570[2-(3,4-Dimethoxy-phenyl)-1-methyl-ethyl]-ethyl amine収率 92%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of 10 g (51.4 mmol) of 3,4-dimethoxyphenylacetone in 50 mL of methanol was cooled to 0° C. and was treated with 50 mL of 2M solution of ethylamine in methanol. To the reaction mixture 11.5 g (0.183 mmol) of sodium cyanoborohydride was added, and the pH of the reaction mixture was adjusted to 6.5-7 by adding glacial acetic acid. The mixture was allowed to stir at room temperature for 4 days. This was concentrated under reduced pressure, and 150 mL of water was added. The pH of the resulting solution was adjusted to 1 using 6 N HCl. This was extracted with 4×150 mL of ether and the organic layers were discarded. The pH of the aqueous layer was adjusted to 14, and the solution was extracted with 6×100 mL of chloroform. The organic layers were combined, dried (Na2SO4) and concentrated to dryness to give 10.6 g (47.4 mmol, 92%) of 2A as a pale yellow oil (M+H, 224).

後処理

  1. concentrationThis was concentrated under reduced pressure, and 150 mL of water
  2. additionwas added
  3. extractionThis was extracted with 4×150 mL of ether
  4. extractionthe solution was extracted with 6×100 mL of chloroform
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-f384dfb7eb134ab891325d8af07c69c5
出典データセット
uspto-grants-2006_06
特許番号
US07060847B2

関連ノート

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