Formaldehyde → HCID 15086796, compound

HRID 2107991Notes

Reaction equation

HRID 2107991 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[CH:10])[C:4]1=[O:11].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[CH2:18]=O.[OH-].[Na+]>C(O)(=O)C.O1CCOCC1>[CH3:1][O:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[C:10][CH2:18][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:4]1=[O:11]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 15086794HCID 15086794, compound

Product 1

HCID 15086796HCID 15086796, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 250 mg of (S)-3-methoxy-1-(2-propynyl)-2-pyrrolidinone, 3.0 ml of dioxane, 0.3 ml of acetic acid, 0.15 g of piperidine, 75 mg of paraformaldehyde and 10 mg of cuprous chloride was heated at reflux for 1 hour then cooled to 0° C. and basified with 1N sodium hydroxide. This mixture was extracted with dichloromethane. The dichloromethane solution was washed with brine, dried and concentrated, giving the desired product, [α]D26 =-43° (dichloromethane).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. extractionThis mixture was extracted with dichloromethane
  4. washThe dichloromethane solution was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e3c0427f31334fb59f50ba7beb973cb2
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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