Triethylamine → HCID 178479308, compound

HRID 2057626Notes

Reaction equation

HRID 2057626 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]=[C:8](Cl)[Cl:9])=[CH:3][CH:2]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C([N:18](CC)CC)C>CCOCC>[ClH:9].[C:4]1([NH:7][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[NH:18])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12145Phenylimidocarbonyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 178479308HCID 178479308, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1.74 g (0.01 mole) of phenyl isocyanide dichloride is added 0.71 g (0.01 mole) of pyrrolidine and 1.01 g (0.01 mole) of triethylamine under N2 in dry ether with stirring and cooling. The resulting mixture is allowed to stir for 1/2 hr and the resultant Et3N.HCl is filtered. The filtrate is added to a saturated solution of anhydrous NH3 in isopropanol. The resulting NH4Cl is filtered and the filtrate is concentrated in vacuo to remove excess ammonia, followed by the addition of dry HCl resulting in crystalline product, N-phenyl-1-pyrrolidinecarboximidamide hydrochloride, m.p. 181°-84° C. after crystallization from methanol-isopropanol.

Workup

  1. temperaturecooling
  2. stirringto stir for 1/2 hr
  3. filtrationthe resultant Et3N.HCl is filtered
  4. additionThe filtrate is added to a saturated solution of anhydrous NH3 in isopropanol
  5. filtrationThe resulting NH4Cl is filtered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customto remove excess ammonia
  8. additionfollowed by the addition of dry HCl resulting in crystalline product, N-phenyl-1-pyrrolidinecarboximidamide hydrochloride, m.p. 181°-84° C.
  9. customafter crystallization from methanol-isopropanol

Sources & evidence

ORD record
ord-b601c8e7f6e245df99fd63a89b495d15
Source dataset
uspto-grants-1980_07
Patent number
US04211867

Reaction notes

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