Methyl vinyl ketone → HCID 86734689, compound

HRID 329021

Reaction equation

HRID 329021 reaction equation
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].[CH2:6]1[C@@H:16]2[C@H:10]([CH:11]=[CH:12][C:13]3[C:14]4[N:15]2[C:17]2[CH:26]=[CH:25][N:24]=[CH:23][C:18]=2[C:19]=4[CH2:20][CH2:21][CH:22]=3)[CH2:9][CH2:8][CH2:7]1>C(O)C>[CH2:6]1[CH:16]2[CH:10]([CH:11]=[CH:12][C:13]3[C:14]4[N:15]2[C:17]2[CH:26]=[CH:25][N:24]=[CH:23][C:18]=2[C:19]=4[CH2:20][CH2:21][CH:22]=3)[CH2:9][CH:8]([CH2:2][CH2:1][C:3](=[O:4])[CH3:5])[CH2:7]1

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketone2×HCID 86734686(+/-)-trans-1,2,3,4,4a,8,9,14a-Octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine

Product 1

HCID 86734689HCID 86734689, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.3 grams of methyl vinyl ketone was added to a solution of 8.3 grams of (±)-trans-1,2,3,4,4a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine in 400 ml. of ethanol. The mixture was permitted to stand at room temperature for four days, after which an additional 2.6 grams of methyl vinyl ketone was added. This mixture was permitted to stand at room temperature for three days, and was then filtered, evaporated to dryness in vacuo, and triturated with pentane. The resulting solid was recrystallized from ethanol to yield 9 grams of the title compound with m.p. 102.5° C.

Workup

  1. waitto stand at room temperature for three days
  2. filtrationwas then filtered
  3. customevaporated to dryness in vacuo
  4. customtriturated with pentane
  5. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-26158a1e72fa4421acd3e10164e0b61a
Source dataset
uspto-grants-1977_04
Patent number
US04018930

Linked notes

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