Ammonia → HCID 67885718, compound

HRID 1587764Notes

Reaction equation

HRID 1587764 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]([CH2:18][C:19]#[N:20])[CH2:7][N:6]1[CH2:21][CH2:22][CH3:23].N.C(OCC)(=[O:27])C>Br.C(O)(=O)C>[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]([CH2:18][C:19]([NH2:20])=[O:27])[CH2:7][N:6]1[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 14822417HCID 14822417, compound

Product 1

HCID 67885718HCID 67885718, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

922 mg of (2-methyl-6-n-propyl-8beta-ergolinyl)-acetonitrile (3 mmol) is dissolved in 15 ml of a 30% solution of HBr in glacial acetic acid and stirred for 3 hours at room temperature. The mixture is mixed with ice, made alkaline with ammonia and shaken with ethyl acetate. The organic phases are dried and concentrated by evaporation. The residue is chromatographed on silica gel with acetone/methanol and crystallized from ethyl acetate, yield 421 mg (43% of theory), [α]D =-67° (0.5% in pyridine).

Workup

  1. additionThe mixture is mixed with ice
  2. customThe organic phases are dried
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with acetone/methanol
  5. customcrystallized from ethyl acetate, yield 421 mg (43% of theory), [α]D =-67° (0.5% in pyridine)

Sources & evidence

ORD record
ord-9d49c0928ae4464eb17843b3f466ce50
Source dataset
uspto-grants-1993_06
Patent number
US05219862

Reaction notes

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