Ammonia → HCID 66585081, compound

HRID 1629989Notes

Reaction equation

HRID 1629989 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]#[N:16])[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:11]1[Cl:23])(C)(C)C.Cl.C=O.N>C(O)C>[Cl:23][C:11]1[N:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:14]2=[C:13]([C:15]#[N:16])[C:12]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 66585000HCID 66585000, compound

Product 1

HCID 66585081HCID 66585081, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 66.9 g (193 mmol) of tert-butyl{2-[2-chloro-4-cyano-3-phenyl-1H-pyrrol-1-yl]ethyl}carbamate in 150 ml of ethanol are added slowly 688 ml (2670 mmol) of aqueous 4N hydrochloric acid solution and the mixture is heated to 90° C. Evolution of gas is rapidly observed, and after 1 hour, the medium is clear. 6.44 g (71.5 mmol) of paraformaldehyde are then added and heating is continued for a further 4 hours. After cooling, the reaction medium is basified slowly by adding aqueous ammonia, the product is extracted with dichloromethane, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give a yellow solid, which is triturated in acetonitrile and then isolated by filtration. The filtrate is concentrated under reduced pressure and the solid residue obtained is triturated in acetonitrile and then isolated by filtration. The two batches of solid are combined to give 30.6 g of 6-chloro-7-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carbonitrile in the form of a beige-coloured powder after drying.

Workup

  1. temperatureheating
  2. waitis continued for a further 4 hours
  3. temperatureAfter cooling
  4. extractionthe product is extracted with dichloromethane
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customto give a yellow solid, which
  8. customis triturated in acetonitrile
  9. customisolated by filtration
  10. concentrationThe filtrate is concentrated under reduced pressure
  11. customthe solid residue obtained
  12. customis triturated in acetonitrile
  13. customisolated by filtration

Sources & evidence

ORD record
ord-2557406a0a3d433e8fb722c0cbf2c7ea
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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