HCID 13559048, compound → HCID 13559056, compound

HRID 569327Notes

Reaction equation

HRID 569327 reaction equation
[C:1]([C:3]1[NH:17][C:16]2[C:18]3[C:4]=1[CH2:5][C@@H:6]1[C@@H:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]([NH:19][C:20](=[O:26])[N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH2:8][N:7]1[CH3:27])#[CH:2]>C(O)C.[Ni]>[CH2:1]([C:3]1[NH:17][C:16]2[C:18]3[C:4]=1[CH2:5][C@@H:6]1[C@@H:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]([NH:19][C:20](=[O:26])[N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[CH2:8][N:7]1[CH3:27])[CH3:2]

Participants

4

Reactant 1

HCID 13559048HCID 13559048, compound

Product 1

HCID 13559056HCID 13559056, compoundYield 384.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

At room temperature and under normal pressure, 140 mg (0.084 mmol) of 3-(2-ethynyl-6-methyl-8α-ergolinyl)-1,1-diethylurea is hydrogenated in 20 ml of ethanol after addition of 0.1 g of Raney nickel within 45 minutes. After the catalyst has been removed by filtration and the solution has been concentrated, the product is recrystallized from ehtanol/hexane, yielding 119 mg of 3-(2-ethyl-6-methyl-8α-ergolinyl)-1,1-diethylurea (84%), mp 165°-168° C., [α]D =+25° (c=0.22 in pyridine).

Workup

  1. customAt room temperature
  2. customAfter the catalyst has been removed by filtration
  3. concentrationthe solution has been concentrated
  4. customthe product is recrystallized from ehtanol/hexane

Sources & evidence

ORD record
ord-33c1bcec011649a4b1c98ccd91a923e1
Source dataset
uspto-grants-1988_03
Patent number
US04731367

Reaction notes

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