Imidazole → HCID 14881507, compound

HRID 2108152Notes

Reaction equation

HRID 2108152 reaction equation
[CH3:1][C@:2]12[C:9]3[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:8]=3[N:7]([CH3:15])[C@H:6]1[N:5]([CH3:16])[CH2:4][CH2:3]2.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].N1C=CN=C1.[NH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>O1CCCC1>[N:35]1([NH:34][C:17](=[O:18])[O:14][C:11]2[CH:10]=[C:9]3[C:8](=[CH:13][CH:12]=2)[N:7]([CH3:15])[C@H:6]2[N:5]([CH3:16])[CH2:4][CH2:3][C@@:2]32[CH3:1])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 20315N-AminomorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 119198Eseroline

Product 1

HCID 14881507HCID 14881507, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Eseroline (3 g) and 1,1'-carbonyldiimidazole (2.3 g) were heated in 150 ml dry tetrahydrofuran (THF) at reflux under nitrogen for one hour. After cooling to +5° C., 0.5 g imidazole was added and a solution of 4-aminomorpholine (3 g) in 30 ml dry THF was dropped into the mixture within 30 minutes. When the addition was complete the mixture was warmed to room temperature and stirred for five hours and thereafter stored in a refrigerator overnight. The THF was evaporated and the oily residue purified by chromatography on neutral alumina with CH2Cl2 /MeOH (95:5). The resulting oil was crystallized from ether/hexane to give a solid (0.6 g) which was combined with 0.5 g obtained from similar experiments and recrystallized from the same solvent mixture. This yielded 1.0 g of crystals, m.p. 115°-117° C.

Workup

  1. temperatureat reflux under nitrogen for one hour
  2. temperatureAfter cooling to +5° C.
  3. additionWhen the addition
  4. customstored in a refrigerator overnight
  5. customThe THF was evaporated
  6. customthe oily residue purified by chromatography on neutral alumina with CH2Cl2 /MeOH (95:5)
  7. customThe resulting oil was crystallized from ether/hexane

Sources & evidence

ORD record
ord-f7adb56dde0747e5a1fa361c09123bd1
Source dataset
uspto-grants-1990_06
Patent number
US04937341

Reaction notes

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