Water → HCID 13770174, compound

HRID 2292240Notes

Reaction equation

HRID 2292240 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][CH:13]=3)[N:9]([CH2:23][CH2:24][CH3:25])[CH2:8]1)=[O:5])[CH3:2].[OH-].[K+].[CH2:30](I)[CH2:31][CH3:32].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]([NH:6][C@H:7]1[CH2:21][C@H:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[N:14]([CH2:30][CH2:31][CH3:32])[CH:13]=3)[N:9]([CH2:23][CH2:24][CH3:25])[CH2:8]1)=[O:5])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 71999Proterguride

Product 1

HCID 13770174HCID 13770174, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, 2 g of 1,1-diethyl-3-(6-n-propyl-8α-ergolinyl)urea, 2.7 g of pulverized KOH, 217 mg of tetrabutylammonium hydrogen sulfate, and 5.5 ml of n-propyl iodide are stirred in 100 ml of absolute tetrahydrofuran for 5 hours at room temperature. After adding 50 ml of H2O, the mixture is extracted with ethyl acetate, rinsed, and dried, thus obtaining 1.8 g (80% of theory) as an oil [α]D =+2.6° (c=0.5 CHCl3)

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washrinsed
  3. customdried
  4. customthus obtaining 1.8 g (80% of theory) as an oil [α]D =+2.6° (c=0.5 CHCl3)

Sources & evidence

ORD record
ord-ff991b2635c44a6c8870aa171f6909d8
Source dataset
uspto-grants-1989_01
Patent number
US04801714

Reaction notes

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