Piperidine → HCID 14626328, compound

HRID 478090Notes

Reaction equation

HRID 478090 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1.N1CCCCC1.[O:25]1[CH2:37][CH:26]1[CH2:27][CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1>C1(C)C=CC=CC=1>[O:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH:31]1[O:30][CH2:29][CH2:28][CH2:27][CH:26]([OH:25])[CH2:37][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 52818947-HydroxyflavoneHCID 198353412-[3-(Oxiran-2-yl)propoxy]oxane

Product 1

HCID 14626328HCID 14626328, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solid mixture of 7-hydroxyflavone (32.0 g, 0.134 mol), piperidine (0.5 ml), and 2-(4,5-epoxypent-1-oxy)tetrahydropyran (50 g, 0.268 mol) was stirred and heated under nitrogen at 100° C. for 14 hours; it became a stirrable mixture after 6 hours heating at 100° C. The cooled reaction mixture was purified through a pad of silica gel eluting with CH2Cl2 initially and then CH2Cl2 --EtOAc (1:1). The resulting solid was stirred with ether and filtered, giving 43.9 g (77% crude yield) of an off-white solid; pure white crystals, mp 110°-112° C., were obtained from recrystallization from toluene.

Workup

  1. customafter 6 hours
  2. temperatureheating at 100° C
  3. customThe cooled reaction mixture
  4. customwas purified through a pad of silica gel eluting with CH2Cl2 initially
  5. stirringThe resulting solid was stirred with ether
  6. filtrationfiltered
  7. customgiving 43.9 g (77% crude yield) of an off-white solid

Sources & evidence

ORD record
ord-6b3b9652ea02441f9dd6f743128730bf
Source dataset
uspto-grants-1989_12
Patent number
US04889941

Reaction notes

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