4-Methylmorpholine → HCID 178457553, compound

HRID 865662Notes

Reaction equation

HRID 865662 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[N:16][C:17]#[N:18])OC2C=CC=CC=2)[CH:2]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]([NH2:29])[CH2:27][CH3:28])[CH:23]=[CH:24][CH:25]=1.CN1CCOCC1>C(O)(C)C>[C:17]([N:16]=[C:8]([NH:29][CH:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=1)[CH2:27][CH3:28])[NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 166406451-(3-Chlorophenyl)propan-1-amineHCID 178512277HCID 178512277, compound

Product 1

HCID 178457553HCID 178457553, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

According to Procedure B, a stirred mixture of N-(3-pyridyl)-N'-cyano-O-phenylisourea (Step 2) (3.00 g, 0.0126 mol), 1-(3-chlorophenyl)propylamine (2.35 g, 0.0139 mol), N-methylmorpholine (30 mL) and isopropanol (20 mL) was refluxed, under nitrogen, for 2.5 hours. The product was purified by silica gel chromatography with 1% to 3% MeOH-CHCl3 and crystallized from MeOH-EtOAc-hexane to give the product: mp 153°-155 ° C.

Workup

  1. temperaturewas refluxed, under nitrogen, for 2.5 hours
  2. customThe product was purified by silica gel chromatography with 1% to 3% MeOH-CHCl3
  3. customcrystallized from MeOH-EtOAc-hexane
  4. customto give the product

Sources & evidence

ORD record
ord-546cd9c6098a4b89ab154d6e0f4d63c1
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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