Cyclohexyl isocyanate → HCID 20511184, compound

HRID 1164503Notes

Reaction equation

HRID 1164503 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[C:18]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][NH:32][CH3:33])[CH2:26][CH2:25]1)=[N:17][N:16]=[CH:15]2>C(Cl)(Cl)Cl>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[C:18]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][CH2:31][N:32]([CH3:33])[C:8]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:9])[CH2:26][CH2:25]1)=[N:17][N:16]=[CH:15]2

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 20511193HCID 20511193, compound

Product 1

HCID 20511184HCID 20511184, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Cyclohexyl isocyanate (0.5 g.) in dry chloroform (5 ml.) was added dropwise to 6,7-dimethoxy-1-[4-[2-(methylamino)ethyl]piperidino]phthalazine (1.0 g.) in dry chloroform (10 ml.) with stirring and ice-water cooling. After further stirring at room temperature (20°) for 1 hour the mixture was concentrated in vacuo, triturated with minimum quantity of ethyl acetate and filtered. The resultant solid was dissolved in methylene chloride (10 ml.), filtered, treated with ethyl acetate (20 ml.) and gently distilled to remove methylene chloride. The residual ethyl acetate solution was left standing in the refrigerator overnight to precipitate crystalline 6,7-dimethoxy-1-[4-[2-(3-cyclohexyl-1-methylureido)ethyl]piperidino]phthalazine (820 mg.), m.p. 204°-206° C.

Workup

  1. stirringAfter further stirring at room temperature (20°) for 1 hour the mixture
  2. concentrationwas concentrated in vacuo
  3. customtriturated with minimum quantity of ethyl acetate
  4. filtrationfiltered
  5. dissolutionThe resultant solid was dissolved in methylene chloride (10 ml.)
  6. filtrationfiltered
  7. additiontreated with ethyl acetate (20 ml.)
  8. distillationgently distilled
  9. customto remove methylene chloride
  10. waitThe residual ethyl acetate solution was left
  11. customstanding in the refrigerator overnight
  12. customto precipitate crystalline 6,7-dimethoxy-1-[4-[2-(3-cyclohexyl-1-methylureido)ethyl]piperidino]phthalazine (820 mg.), m.p. 204°-206° C.

Sources & evidence

ORD record
ord-37c80bcd4d0040b1a8b236c62e812ee2
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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