Methyl iodide → HCID 88411977, compound

HRID 1078255Notes

Reaction equation

HRID 1078255 reaction equation
O1CCN(CC2[NH:22][C:21]3[C:23]4C=2C[C@@H:11]2[C@@H:16]([C:17]=4[CH:18]=[CH:19][CH:20]=3)[CH2:15][C@H:14]([NH2:24])[CH2:13][N:12]2[CH2:25][CH2:26][CH3:27])CC1.[CH3:28]I.[CH:30]([O:33]C(C)C)(C)C.[Na].[O:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>CO>[CH3:28][O:38][CH2:42][C:41]1[NH:22][C:21]2[C:23]3[C:40]=1[CH2:39][C@@H:11]1[C@@H:16]([C:17]=3[CH:18]=[CH:19][CH:20]=2)[CH2:15][C@H:14]([NH:24][CH:30]=[O:33])[CH2:13][N:12]1[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 7914Diisopropyl EtherHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 15069961HCID 15069961, compound

Product 1

HCID 88411977HCID 88411977, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.1 g of 2-morpholinomethyl-6-n-propyl-8alpha-ergolinylamine (3 mmol) is formylated as described in example 4, then mixed, in 50 ml of tetrahydrofuran, with 2 ml of methyl iodide and stirred for 20 hours at room temperature. Then it is cooled in an ice bath and mixed with diisopropyl ether for completion of the crystallization. The crystals are isolated and dissolved in 30 ml of methanol. At the same time, a methylate solution, in which the solution of the quartenary salt is instilled at 0° C., is prepared from 230 mg of sodium (10 mmol) in 20 ml of methanol. After 15 minutes stirring at 0° C. and 30 minutes at room temperature, ice is added and extraction is performed with dichloromethane. The organic phases are dried and concentrated by evaporation, the residue is chromatographed on silica gel with dichloromethane and methanol, yield 470 mg (48% of theory).

Workup

  1. temperatureThen it is cooled in an ice bath
  2. customThe crystals are isolated
  3. customis instilled at 0° C.
  4. stirringAfter 15 minutes stirring at 0° C. and 30 minutes at room temperature
  5. additionice is added
  6. extractionextraction
  7. customThe organic phases are dried
  8. concentrationconcentrated by evaporation
  9. customthe residue is chromatographed on silica gel with dichloromethane and methanol, yield 470 mg (48% of theory)

Sources & evidence

ORD record
ord-cc77996d52ee456991f077b016f01d11
Source dataset
uspto-grants-1996_08
Patent number
US05547958

Reaction notes

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