O-Methyltyramine → HCID 20227987, compound

HRID 1731584Notes

Reaction equation

HRID 1731584 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH2:36])=[CH:30][CH:29]=1.[Cl:37][C:38]1[CH:39]=[C:40]([CH:46]=[CH:47][CH:48]=1)[CH:41]([OH:45])[C:42](O)=[O:43]>CN(C)C=O>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][NH:36][C:42](=[O:43])[CH:41]([OH:45])[C:40]2[CH:46]=[CH:47][CH:48]=[C:38]([Cl:37])[CH:39]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 4657O-MethyltyramineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 859813-Chloromandelic acid

Product 1

HCID 20227987HCID 20227987, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dicyclohexylcarbodiimide (2.00 g) in N,N-dimethylformamide (10 ml) was added to a solution of 1-hydroxybenzotriazole (1.37 g), 2-(4-methoxyphenyl)ethanamine (1.51 g) and 3-chloromandelic acid (1.86 g) in N,N-dimethylformamide (40 ml) and the mixture stirred for 18 hours, filtered then evaporated to dryness. The residue was dissolved in dichloromethane, washed with aqueous 4M hydrochloric acid and sodium bicarbonate solution, dried (magnesium sulphate), filtered and evaporated to dryness to give the title compound as an oil which was used without further purification.

Workup

  1. filtrationfiltered
  2. customthen evaporated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with aqueous 4M hydrochloric acid and sodium bicarbonate solution
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-ebbbb72971fc43148ca325651433a408
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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