(R)-Octopamine → HCID 70603056, compound

HRID 1283971Notes

Reaction equation

HRID 1283971 reaction equation
[CH:1]1[C:6]([C@@H:7]([OH:10])[CH2:8][NH2:9])=[CH:5][CH:4]=[C:3]([OH:11])[CH:2]=1.[C:12]([C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21](=O)[CH3:22])=[CH:17][CH:16]=1)(=[O:14])[NH2:13]>[Pt]=O.C(O)C>[OH2:10].[C:12]([C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]([NH:9][CH2:8][CH:7]([C:6]2[CH:5]=[CH:4][C:3]([OH:11])=[CH:2][CH:1]=2)[OH:10])[CH3:22])=[CH:17][CH:16]=1)(=[O:14])[NH2:13].[C:12]([C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]([NH:9][CH2:8][CH:7]([C:6]2[CH:5]=[CH:4][C:3]([OH:11])=[CH:2][CH:1]=2)[OH:10])[CH3:22])=[CH:17][CH:16]=1)(=[O:14])[NH2:13]

Participants

5

Reactant 2

HCID 440266(R)-OctopamineHCID 128126714-(2-Oxopropoxy)benzamide

Product 1

HCID 70603056HCID 70603056, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of DL-octopamine (4.6 g.), 4-carbamoylphenoxy acetone (5.8 g.) and ethanol (150 ml.) was boiled under reflux for 8 hours in the presence of molecular sieves, then hydrogenated over platinum oxide at 50 p.s.i. and 50°C. Filtration and evaporation in vacuo of the filtrate gave a viscous oil which was triturated with ether to provide a semi-solid material. This material was then triturated with ethanol and the residual white solid crystallized from aqueous dimethylformamide to afford DL-2-[2-(4-carbamoyl-phenoxy)-1-methylethylamino]-1-(4-hydroxyphenyl)ethanol hemihydrate (2.0 g.), m.p. 195-198°C.

Workup

  1. temperatureunder reflux for 8 hours in the presence of molecular sieves
  2. custom50°C
  3. filtrationFiltration and evaporation in vacuo of the filtrate
  4. customgave a viscous oil which
  5. customwas triturated with ether
  6. customto provide a semi-solid material
  7. customThis material was then triturated with ethanol
  8. customthe residual white solid crystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-8cdd0e7dc1324f2295b5e33c4d0dd0d5
Source dataset
uspto-grants-1976_08
Patent number
US03976783

Reaction notes

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