Triethylamine → HCID 23169248, compound

HRID 466620Notes

Reaction equation

HRID 466620 reaction equation
[CH3:1][N:2]1[C:6](=[CH2:7])[C:5]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[O:4][C:3]1=[O:13].C(N(CC)CC)C.[C:21]([C:24]1[CH:37]=[CH:36][C:35]2[S:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:38][CH2:39][CH2:40]Br)[C:26]=2[CH:25]=1)(=[O:23])[CH3:22]>C(C(C)=O)C(C)C>[C:21]([C:24]1[CH:37]=[CH:36][C:35]2[S:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:38][CH2:39][CH2:40][CH:8]3[CH2:9][NH:10][CH2:11][CH2:12][C:5]43[O:4][C:3](=[O:13])[N:2]([CH3:1])[C:6]4=[CH2:7])[C:26]=2[CH:25]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10154328HCID 10154328, compoundHCID 19814298HCID 19814298, compound

Product 1

HCID 23169248HCID 23169248, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 7.3 g of 3-methyl-4-methylene-2-oxo-1-oxa-3,8-diazaspiro[4,5]decane, 9 ml of anhydrous triethylamine, 22.0 g of 3-(2-acetyl-10H-phenothiazin-10-yl)-propyl bromide and 80 ml of methyl isobutyl ketone is refluxed under argon while stirring for 6 hours. After cooling down the organic phase is washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The crude product obtained is purified by chromatography on a silica gel column by using first chloroform and then ethyl acetate as eluating agent. After combining the ethyl acetate eluate is evaporated under reduced pressure and the residue is recrystallized from ethanol to give the title compound in 84.5% yield, m.p.: 105°-106° C.

Workup

  1. temperatureis refluxed under argon
  2. temperatureAfter cooling down the organic phase
  3. washis washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe crude product obtained
  7. customis purified by chromatography on a silica gel column
  8. customis evaporated under reduced pressure
  9. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-bbcfbaac8d5843fc9d0fdb5702182674
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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