1,1'-Carbonyldiimidazole → HCID 178456165, compound

HRID 1756534Notes

Reaction equation

HRID 1756534 reaction equation
[CH:1]([N:4]1[C:18]2[C:19]3[C:6]([CH2:7][C@@H:8]4[C@@H:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:12][C@@H:11]([C:20](O)=[O:21])[CH2:10][N:9]4[CH3:23])=[CH:5]1)([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:36][C@H:37]1[CH2:42][CH2:41][C@H:40]([NH2:43])[CH2:39][CH2:38]1>CN(C)C=O>[NH2:36][C@H:37]1[CH2:42][CH2:41][C@H:40]([NH:43][C:20]([C@@H:11]2[CH2:12][C@H:13]3[C@@H:8]([CH2:7][C:6]4[C:19]5[C:18](=[CH:17][CH:16]=[CH:15][C:14]3=5)[N:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=4)[N:9]([CH3:23])[CH2:10]2)=[O:21])[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1825776-Methyl-1-(propan-2-yl)ergoline-8-carboxylic acidHCID 178511674HCID 178511674, compound

Product 1

HCID 178456165HCID 178456165, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 10.07 g of (8β)-1-isopropyl-6-methylergoline-8-carboxylic acid in 300 ml of dimethylformamide were added 5.5 g of 1,1'-carbonyldiimidazole. After stirring at room temperature for 3 hours, this solution was added to a solution of 36.9 g of trans-1,4-diaminocyclohexane in 600 ml of dimethylformamide; the addition was made dropwise over a period of 3.5 hours. After the addition was complete, the reaction mixture was allowed to stir at room temperature overnight. The solution was poured into 4 liters of ice and the aqueous solution extracted 8 times with 500 ml each of methylene chloride. The combined organic extracts were washed three times with water, one time with a saturated sodium chloride solution, dried over sodium sulfate, and then concentrated in vacuo to provide 12.5 g of title compound as a yellow solid. A portion of this free base material was treated with p-toluenesulfonic acid in ethyl acetate/ethanol to provide the ditosylate salt, m.p. 236°-239° C. NMR, MS.

Workup

  1. additionthe addition
  2. waitwas made dropwise over a period of 3.5 hours
  3. additionAfter the addition
  4. stirringto stir at room temperature overnight
  5. extractionthe aqueous solution extracted 8 times with 500 ml each of methylene chloride
  6. washThe combined organic extracts were washed three times with water, one time with a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ecd0638e5174e3096e29e0cd0a82e0b
Source dataset
uspto-grants-1995_08
Patent number
US05441961

Reaction notes

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