Formaldehyde → Acetamide, N-methyl-N-[4-[3-(hydroxymethyl)pyrrolidinyl]-2-butynyl]-

HRID 2107989Notes

Reaction equation

HRID 2107989 reaction equation
[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH3:8][N:9]([CH2:13][C:14]#[CH:15])[C:10](=[O:12])[CH3:11].[CH2:16]=O.[OH-].[Na+]>O.O1CCOCC1.C(O)(=O)C>[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:16][C:15]#[C:14][CH2:13][N:9]([CH3:8])[C:10](=[O:12])[CH3:11])[CH2:4]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 29033Acetamide, N-methyl-N-[2-propynyl]-HCID 113554473-Methoxypyrrolidine

Product 1

HCID 606285Acetamide, N-methyl-N-[4-[3-(hydroxymethyl)pyrrolidinyl]-2-butynyl]-Yield 75.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 365 mg of (racemic)-3-methoxypyrrolidine, 480 mg of N-methyl-N-propargyl acetamide, 180 mg of paraformaldehyde, 0.6 ml of acetic acid, 20 ml of dioxane and cuprous chloride catalyst was stirred at reflux under argon for 1 hour. The mixture was treated with 3 ml of 5N sodium hydroxide and 2 ml of water and extracted twice with dichloromethane. The extracts were combined, concentrated and purified by chromatography (alumina), giving 610 mg of the desired product.

Workup

  1. temperatureat reflux under argon for 1 hour
  2. extractionextracted twice with dichloromethane
  3. concentrationconcentrated
  4. custompurified by chromatography (alumina)

Sources & evidence

ORD record
ord-53a0cdb4a40848ddae9c023c49fe6a76
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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