Cyclohexanecarbonyl chloride → HCID 23456604, compound

HRID 1680503Notes

Reaction equation

HRID 1680503 reaction equation
[C:1]1(=[O:15])[CH:6]2[C:7]3[C:12]([C:13](=[O:14])[N:5]2[CH2:4][CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH:16]1([C:22](Cl)=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[CH:16]1([C:22]([N:2]2[CH2:3][CH2:4][N:5]3[C:13](=[O:14])[C:12]4[C:7]([CH:6]3[C:1]2=[O:15])=[CH:8][CH:9]=[CH:10][CH:11]=4)=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 12901715HCID 12901715, compound

Product 1

HCID 23456604HCID 23456604, compoundYield 19.2%

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4-dihydropyrazino[2,1-a]isoindole-1,6(2H, 10bH)-dione (6.0 g, 0.03 mol, described in Example 6) and cyclohexylcarbonyl chloride (6.5 g, 0.045 mol) is stirred at 120° C. for 6.5 hr and evaporated. The residue is chromatographed on silica gel using 20% acetone in benzene and the eluates are evaporated. The residue is crystallized from acetone to obtain 2-(cyclohexylcarbonyl)-1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindole-1,6-dione (1.8 g), mp 167°-172° C., Anal. Calc'd. for C18H20N2O3 : C, 69.21% H, 6.45% N, 8.97% and Found: C, 69.25% H, 6.47% N, 8.93%.

Workup

  1. customevaporated
  2. customThe residue is chromatographed on silica gel using 20% acetone in benzene
  3. customthe eluates are evaporated
  4. customThe residue is crystallized from acetone

Sources & evidence

ORD record
ord-fff4d0b991bf4ad2b3a66ddb94bf1a49
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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