Cyclohexanone → HCID 89483138, compound

HRID 1772185Notes

Reaction equation

HRID 1772185 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:3]=1.[CH:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1(=O)CCCCC1>C(O)(=O)C>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[C:3]=1[C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1.[CH:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 89482785HCID 89482785, compound

Product 1

HCID 89483138HCID 89483138, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 500 mL of reaction flask were added the compound of Example 4C (47.86 g, 159.32 mmol), cyclohexanone (31.27 g, 318.64 mmol) and acetic acid (300 mL). The mixture was heated to 50° C. to 60° C. under nitrogen atmosphere. The reaction was kept overnight. The reaction was stopped and cooled to room temperature. Acetic acid was rotary-evaporated to obtain a crude product. The crude product was separated by column chromatography to give 45.53 g of the title compound as white solid. Yield: 75.1%. MS (ESI): m/z 381 (M+H)+

Workup

  1. customTo a 500 mL of reaction flask
  2. temperatureThe mixture was heated to 50° C. to 60° C. under nitrogen atmosphere
  3. customAcetic acid was rotary-evaporated
  4. customto obtain a crude product
  5. customThe crude product was separated by column chromatography

Sources & evidence

ORD record
ord-8cb662c8734a472faa08fe066efdefa1
Source dataset
uspto-grants-2016_02
Patent number
US09249172B2

Reaction notes

Loading…