HCID 9805027, compound → HCID 19420731, compound

HRID 863835Notes

Reaction equation

HRID 863835 reaction equation
[ClH:1].[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:34]=[CH:33][C:14]([CH2:15][O:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][O:22][CH2:23][C:24]#[C:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[CH:13][CH:12]=1>CO.[Pd]>[ClH:1].[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:34]=[CH:33][C:14]([CH2:15][O:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 9805027HCID 9805027, compound

Product 1

HCID 19420731HCID 19420731, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-[3-(4-methylphenyl)prop-2-ynyloxy]ethanamine hydrochloride (125 mg) is dissolved in MeOH (12 ml) in an argon atmosphere and then 27 mg Pd/C catalyst is added. H2 is bubbled into the reaction mixture for 1 minute and stirred under H2 for 20 minutes. The mixture is purged with argon and filtered through celite and washed with MeOH and THF. Several drops of HCl/EtOH are added until acidic and the mixture concentrated to dryness to obtain N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-[3-(4-methyl-phenyl)propoxy]ethanamine hydrochloride as a white solid. (m.p. 138°-139° C.).

Workup

  1. customH2 is bubbled into the reaction mixture for 1 minute
  2. customThe mixture is purged with argon
  3. filtrationfiltered through celite
  4. washwashed with MeOH and THF
  5. additionSeveral drops of HCl/EtOH are added until acidic and the mixture
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-af90ca5bbc9d44d6af0f07b9a2d63707
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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