HCID 13079730, compound → HCID 20610366, compound

HRID 1731100Notes

Reaction equation

HRID 1731100 reaction equation
[CH:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:30]=1[O:31]CC1C=CC=CC=1)[CH:7]([OH:27])[CH2:8][N:9](CC1C=CC=CC=1)[CH:10]([CH3:19])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[O:2]>[C].[Pd].C(O)C>[CH:1]([NH:3][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:30]=1[OH:31])[CH:7]([OH:27])[CH2:8][NH:9][CH:10]([CH3:19])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[O:2]

Participants

4

Reactant 1

HCID 13079730HCID 13079730, compound

Product 1

HCID 20610366HCID 20610366, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 50 ml. of ethanol there was dissolved 1.62 g. of 3-formylamino-4-benzyloxy-α-[N-benzyl-N-(1-methyl-2-p-tolylethyl)aminomethyl]benzyl alcohol prepared by the procedure in Reference Example 10 and after adding to the solution 0.3 g. of 10% palladium carbon, the catalytic reduction was conducted at normal temperature and pressure until 154 ml. of hydrogen was absorbed. The catalyst was filtered off and after adding to the remaining ethanol solution 8 ml. of water, and 186 mg. of fumaric acid, the solvent was removed from the resultant solution under a reduced pressure. The residue was dissolved in ethanol and benzene was added to the solution until the solution became slightly turbid. When the system was allowed to stand in a refrigerator, 550 mg. of a white crystalline material was formed. The crystals were recovered and recrystallized from ethanol-benzene to give 3-formylamino-4-hydroxy-α-[N-(1-methyl-2-p-tolylethyl)aminomethyl]benzyl alcohol . 1/2 fumarate . 1/2 hydrate melting at 132°-133° C. (decomposed).

Workup

  1. customof hydrogen was absorbed
  2. filtrationThe catalyst was filtered off
  3. additionafter adding to the remaining ethanol solution 8 ml
  4. customof fumaric acid, the solvent was removed from the resultant solution under a reduced pressure
  5. dissolutionThe residue was dissolved in ethanol
  6. additionbenzene was added to the solution until the solution
  7. customof a white crystalline material was formed
  8. customThe crystals were recovered
  9. customrecrystallized from ethanol-benzene

Sources & evidence

ORD record
ord-bec863485c644c09951ab8631c002fa6
Source dataset
uspto-grants-1976_11
Patent number
US03994974

Reaction notes

Loading…