Diethyl Ether → HCID 4010221, compound

HRID 1731096Notes

Reaction equation

HRID 1731096 reaction equation
C([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH:13]([OH:26])[CH2:14][N:15](CC2C=CC=CC=2)[CH:16]([CH3:18])[CH3:17])=[CH:11][C:10]=1[NH:29][CH:30]=[O:31])C1C=CC=CC=1.CCOCC>C(O)C.[C].[Pd]>[CH:30]([NH:29][C:10]1[CH:11]=[C:12]([CH:27]=[CH:28][C:9]=1[OH:8])[CH:13]([OH:26])[CH2:14][NH:15][CH:16]([CH3:18])[CH3:17])=[O:31]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 13043272HCID 13043272, compound

Product 1

HCID 4010221HCID 4010221, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×

Procedure

In 20 ml. of ethanol there was dissolved 1.4 g. of 4-benzyloxy-3-formylamino-α-(N-benzyl-N-isopropylaminomethyl)-benzyl alcohol and after adding to the solution 0.2 g. of 10% palladium carbon, the catalytic reduction was carried out at normal temperature and pressure. After 165 ml. of hydrogen was absorbed, the reaction was stopped. The catalyst was filtered off, the solvent was distilled off under reduced pressure, and then the residue thus formed was dissolved in a small amount of ethanol. Thereafter, when a small amount of ether was added to the solution and the solution was allowed to stand, a crystalline material was formed. By recovering the crystalline material by filtration, 0.7 g. of 3-formylamino-4-hydroxy-α-(isopropylaminomethyl)benzyl alcohol was obtained.

Workup

  1. customof hydrogen was absorbed
  2. filtrationThe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue thus formed
  5. customa crystalline material was formed
  6. customBy recovering the crystalline material
  7. filtrationby filtration, 0.7 g

Sources & evidence

ORD record
ord-4c34be4aeb6b45f681799ec516354598
Source dataset
uspto-grants-1976_11
Patent number
US03994974

Reaction notes

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