Cyclopentylamine → HCID 15067920, compound

HRID 2106721Notes

Reaction equation

HRID 2106721 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]([NH:22]N)=[O:21])[CH2:10][N:9]4[CH3:24])=[CH:5]1)([CH3:3])[CH3:2].N([O-])=O.[Na+].C(=O)(O)[O-].[Na+].[CH:34]1(N)[CH2:38][CH2:37][CH2:36][CH2:35]1>Cl.CN(C=O)C.O>[CH:34]1([NH:22][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]([CH3:3])[CH3:2])[CH:5]=4)[N:9]([CH3:24])[CH2:10]2)=[O:21])[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

8

Reactant 4

HCID 2906CyclopentylamineHCID 516892Sodium BicarbonateHCID 14011082HCID 14011082, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15067920HCID 15067920, compoundYield 32.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.26 g (0.01 mol) of (8β)-1-isopropyl-6-methylergoline-8-hydrazide dissolved in 25 ml of hydrochloric acid and 100 ml of water at a temperature of about 5° C. was added 55 ml of a solution of 0.2N sodium nitrite dropwise over a period of about five minutes. The resulting mixture was stirred at room temperature for approximately five minutes and sufficient saturated sodium bicarbonate solution was added dropwise until the pH of the mixture was basic. The mixture was extracted with three 200 ml portions of diethyl ether. The organic extracts were combined, dried over anhydrous magnesium sulfate and filtered. To the resulting filtrate was added a solution of 2.55 g (0.03 mol) of cyclopentylamine dissolved in 50 ml of DMF. The resulting mixture was stored at a temperature of about 5° C. overnight. The solvent was decanted from the resulting oil. The oil was slurried in acetonitrile and the solvent was again decanted. The resulting solid was recrystallized from acetonitrile to provide 1.23 g of the desired compound. m/e=379.

Workup

  1. extractionThe mixture was extracted with three 200 ml portions of diethyl ether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customwas stored at a temperature of about 5° C. overnight
  5. customThe solvent was decanted from the resulting oil
  6. customthe solvent was again decanted
  7. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-88bdac51b54b44fa980f485ff1bdccc2
Source dataset
uspto-grants-1990_06
Patent number
US04931447

Reaction notes

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