Formaldehyde → HCID 86746962, compound

HRID 1587754Notes

Reaction equation

HRID 1587754 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:19][C@H:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][CH:11]=3)[N:7]([C:21]#[N:22])[CH2:6]1)=[O:4].Cl.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C=O.[C:32](=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:19][C@H:18]2[C@@H:8]([CH2:9][C:10]3[C:20]4[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=4)[NH:12][C:11]=3[CH2:32][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:7]([C:21]#[N:22])[CH2:6]1)=[O:4]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 197884Morpholine, hydrochloride (1:1)HCID 10108547HCID 10108547, compound

Product 1

HCID 86746962HCID 86746962, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

3.54 g of 6-cyano-8beta-ergoline-carboxylic acid methyl ester (12 mmol), 9.46 g of morpholine hydrochloride (77 mmol) and 1.77 g of paraformaldehyde (59 mmol) are heated in 90 ml of dimethylformamide for 30 minutes at 100° C. After cooling, the mixture is poured on ice, made alkaline with sodium carbonate solution and shaken out five times with toluene. The organic phases are washed with water, dried with sodium sulfate and concentrated by evaporation. The precipitated crystals are suctioned off, yield 4.71 g (quantitative). The substance is chromatographed on silica gel with dichloromethane/methanol (98:1 and 9:1), 3.05 g (64% of theory) is isolated. The substance can be crystallized from dichloromethane/diisopropylether, the pure substance is obtained in 50% yield. [α]D =+33.4° (0.5% in chloroform).

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured on ice
  3. washThe organic phases are washed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe substance is chromatographed on silica gel with dichloromethane/methanol (98:1 and 9:1)
  7. custom3.05 g (64% of theory) is isolated
  8. customThe substance can be crystallized from dichloromethane/diisopropylether
  9. customthe pure substance is obtained in 50% yield

Sources & evidence

ORD record
ord-7b7d1b2fbcb44348b05c676c447bcda8
Source dataset
uspto-grants-1993_06
Patent number
US05219862

Reaction notes

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