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

HRID 1651346노트

반응식

HRID 1651346 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-398904e3aaf54b5f9d006cdb0dbc4cbe
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04927968

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