Hydrochloric Acid → 1-Amino-2-[3-(3-hydroxymethylphenoxy)propylamino]-1-cyclobutene-3,4-dione

HRID 1651346ノート

反応式

HRID 1651346 の反応式
[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[O:20])[CH:14]=1.N1CCCCC1.Cl.O>C(O)C.[Pd]>[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8082PiperidineHCID 230519081-Amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione

生成物 1

HCID 230519061-Amino-2-[3-(3-hydroxymethylphenoxy)propylamino]-1-cyclobutene-3,4-dione収率 71.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A suspension of 1-amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione (2.09 g, 7.29 mmoles), piperidine (0.8 mL, 690 mg, 8.1 mmoles) and 200 mg of 10% Pd/C in 300 mL of 95% ethanol was shaken on a Parr hydrogenator at 50 psi for 4 hours. To the resultant mixture with stirring was added 8.3 mL of aqueous 1.0N HCl and 25 mL of water. The reaction mixture was filtered through diatomaceous earth and the filtrate was evaporated under reduced pressure. The solid residue was treated with acetone and allowed to stand at 0° C. for 18 hours. The mixture was filtered and the solid dried to give 1.437 g of product containing a small amount of starting aldehyde; mp=207°-212° C.

後処理

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe filtrate was evaporated under reduced pressure
  3. additionThe solid residue was treated with acetone
  4. waitto stand at 0° C. for 18 hours
  5. filtrationThe mixture was filtered
  6. customthe solid dried

出典と根拠

ORDレコード
ord-398904e3aaf54b5f9d006cdb0dbc4cbe
出典データセット
uspto-grants-1990_05
特許番号
US04927968

反応ノート

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