Hydrochloric Acid → HCID 68426089, compound

HRID 1785616Notes

Reaction equation

HRID 1785616 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][NH2:11])=[CH:5][CH:4]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].Cl>C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[N:12]([CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[C:23](=[O:24])[NH:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 68427487HCID 68427487, compound

Product 1

HCID 68426089HCID 68426089, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 1-(R)-(4-methoxyphenyl)-N1-[2-(4-methoxyphenyl)ethyl]ethane-1,2-diamine (446 g, 1.48 mol) in ethyl acetate (2.25 L) is placed in a water bath and 1,1′-carbonyldiimidazole (264 g, 1.62 mol) is added in portions. The reaction is then heated to reflux for 1.5 hours after which the solution is cooled, treated with 1N HCl (2×1.5 L), brine (2×1.5 L), dried over Na2SO4 and set aside in the cold. After standing the precipitate which forms is removed by filtration and the solvent removed under reduced pressure to afford 468 g (96% yield) of the desired product. Chiral HPLC of the product thus obtained to have 99.5% of the desired (R) enantiomer present.

Workup

  1. temperatureThe reaction is then heated
  2. temperatureto reflux for 1.5 hours after which the solution
  3. temperatureis cooled
  4. dry with materialdried over Na2SO4
  5. customforms is removed by filtration
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-89730026afe84821898c198094e13e2c
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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