1-Naphthol → HCID 13423956, compound

HRID 1980249Notes

Reaction equation

HRID 1980249 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:10]2([O:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([OH:25])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1>[C:15]1([O:25][CH2:11][C:10]2([OH:12])[CH2:13][CH2:14][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9]2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 70051-NaphtholHCID 111948055-Benzyl-1-oxa-5-azaspiro[2.4]heptane

Product 1

HCID 13423956HCID 13423956, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 18.9 g (0.1 mole) of 5-benzyl-1-oxa-5-azaspiro[2.4]heptane and 15.6 g (0.11 mole) of 1-naphthol was heated to 115° C. to form a homogenous melt, which was stirred with a magnetic stirrer for 2 hours. Upon cooling, a paste-like material formed. The reaction mixture was dissolved in benzene, filtered and ligroin added to the filtrate until cloudy. The suspension was warmed to solution and allowed to stand in the refrigerator overnight. The precipitate was collected by filtration to give 20.2 g (60%) of crude material. A portion of this solid was recrystallized from 190 ethanol to give a white crystalline solid, m.p. 129.5°-130° C.

Workup

  1. customto form a homogenous melt, which
  2. temperatureUpon cooling
  3. customa paste-like material formed
  4. filtrationfiltered
  5. additionligroin added to the filtrate until cloudy
  6. temperatureThe suspension was warmed to solution
  7. customto stand in the refrigerator overnight
  8. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c1c74ebb996042eda9459983babde584
Source dataset
uspto-grants-1985_04
Patent number
US04508724

Reaction notes

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