Sodium Cyanate → HCID 19896749, compound

HRID 1196878Notes

Reaction equation

HRID 1196878 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[O-:24][C:25]#[N:26].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:25]([NH2:26])=[O:24])[CH2:14][CH:13]2[CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 10222149HCID 10222149, compound

Product 1

HCID 19896749HCID 19896749, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 1-[(3,4-dichlorophenyl)acetyl]-2-(1-pyrrolidinylmethyl) piperazine (200 mg) in acetic acid (0.5 ml) and water (1 ml) was treated with a solution of sodium cyanate (73 mg) in water (0.5 ml). The resulting solution was stirred at room temperature for 2 h. The solvent was removed in vacuo, the residue was basified with aqueous 2N sodium carbonate solution and extracted with dichloromethane (2×25 ml). The combined organic extracts were dried and evaporated to give a foam (206 mg) which was purified by flash column chromatography eluting with dichloromethane:methanol:0.880 NH3 (200:8:1) to give a solid (120 mg). Crystallisation from ethyl acetate/methanol gave the title compound as a solid (58 mg) m.p. 206°-209° C.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted with dichloromethane (2×25 ml)
  3. customThe combined organic extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-0bf34058cda64062a3768d9e780cb83e
Source dataset
uspto-grants-1992_05
Patent number
US05116842

Reaction notes

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