Hydrochloric Acid → HCID 178484576, compound

HRID 1441372Notes

Reaction equation

HRID 1441372 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)=[O:4].Cl.O1CCOCC1.[N:25]#[C:26][NH2:27]>CCO.C(#N)C>[CH3:1][N:2]([CH3:17])[C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:26]([NH2:27])=[NH:25])=[CH:14][CH:15]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 312751,4-DioxaneHCID 68686439(S)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide

Product 1

HCID 178484576HCID 178484576, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To (S)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide (Method 53; 0.67 g) was added acetonitrile (20 ml) and EtOH (2 ml). HCl in dioxane (0.86 ml, 3.48 mmol) was added and the reaction was stirred for 10 minutes, HCl salt precipitated. Cyanamide (0.2 g, 4.9 mmol) was added and the reaction was heated at reflux over the weekend. The black reaction was filtered and the black HCl salt was dissolved in water (5 ml) and basified with NaHCO3 (20 ml) solution. No solid was observed; the aqueous was further basified to pH 14 with KOH, extracted with DCM (2×100 ml), dried and solvent removed in vacuo to yield the title compound as a black gum (0.50 g, 63%). M/z 276.

Workup

  1. customHCl salt precipitated
  2. temperaturethe reaction was heated
  3. temperatureat reflux over the weekend
  4. customThe black reaction
  5. filtrationwas filtered
  6. dissolutionthe black HCl salt was dissolved in water (5 ml)
  7. extractionextracted with DCM (2×100 ml)
  8. customdried
  9. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-e616d8ed757440d0b10109c81c36ef9a
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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