Ammonia → HCID 15069926, compound

HRID 248883Notes

Reaction equation

HRID 248883 reaction equation
[CH3:1][C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH2:18])[CH2:7][N:6]1[CH2:19][CH2:20][CH3:21].[CH3:22][O:23][CH2:24][C:25](Cl)=[O:26].N>N1C=CC=CC=1>[CH3:1][C:2]1[NH:16][C:15]2[C:17]3[C:3]=1[CH2:4][C@@H:5]1[C@@H:10]([C:11]=3[CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:18][C:25](=[O:26])[CH2:24][O:23][CH3:22])[CH2:7][N:6]1[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 96623Methoxyacetyl chlorideHCID 15069916HCID 15069916, compound

Product 1

HCID 15069926HCID 15069926, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

849 mg of 2-methyl6n-propyl-8alpha-ergolinylamine (3 mmol) is dissolved in 20 ml of pyridine and stirred with 2.28 ml of methoxy acetyl chloride (30 mmol) for 30 minutes at room temperature. Then it is poured onto ice, stirred for 15 minutes, make alkaline with ammonia and extracted with dichloromethane. The organic phases are dried and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/methanol and crystallized from ethyl acetate. Yield 420 mg (40% of theory), [α]D =+24° (0.5% in chloroform).

Workup

  1. additionThen it is poured onto ice
  2. extractionextracted with dichloromethane
  3. customThe organic phases are dried
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with ethyl acetate/methanol
  6. customcrystallized from ethyl acetate
  7. customYield 420 mg (40% of theory), [α]D =+24° (0.5% in chloroform)

Sources & evidence

ORD record
ord-4dba6cf13e9b498398b42fe2ae312048
Source dataset
uspto-grants-1993_05
Patent number
US05212178

Reaction notes

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