Benzenamine hydrochloride (1:1) → HCID 135492826, compound

HRID 1588251Notes

Reaction equation

HRID 1588251 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]1([N+:21]#[C-:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[O-:23][C:24]#[N:25].[K+].Cl.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O.C(OCC)C.CCCCCC>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([N:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:24](=[O:23])[NH:25][C:22]2=[N:21][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8870Benzenamine hydrochloride (1:1)HCID 192201-Benzyl-4-piperidoneHCID 79129Cyclohexyl isocyanideHCID 11378442Potassium cyanate

Product 1

HCID 135492826HCID 135492826, compoundYield 27%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared by the method of Ugi, et al. (Liebig's Ann., 1963, 666:54-61). 1-Benzyl-4-piperidinone (94.5 g, 0.5 mol) and cyclohexylisonitrile (54.5 g, 0.45 mol), both commercially available from Aldrich Chemical Company, were dissolved in 250 mL of methanol at ambient temperature. A solution of potassium cyanate (40.5 g, 0.5 mol) in 100 mL of water was added in one portion with stirring. Aniline hydrochloride was added in portions over a 45 minute period and the reaction mixture was allowed to stir at ambient temperature overnight. Hexane and diethyl ether were added to the reaction mixture until a solid formed. The solid was filtered and washed with diethyl ether and water. The solid was then triturated with four 1 L portions of boiling water and crystallized from methanol to give 50.6 g (27% yield) of the title compound, m.p. 208°-210° C.

Workup

  1. customThe title compound was prepared by the method of Ugi, et al. (Liebig's Ann., 1963, 666:54-61)
  2. stirringto stir at ambient temperature overnight
  3. customformed
  4. filtrationThe solid was filtered
  5. washwashed with diethyl ether and water
  6. customThe solid was then triturated with four 1 L portions of boiling water
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-3262c7e48c9b4d989aeb8783288daa22
Source dataset
uspto-grants-1993_06
Patent number
US05221675

Reaction notes

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