Formaldehyde → HCID 21430573, compound

HRID 1730369Notes

Reaction equation

HRID 1730369 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]=O.[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[C:22]#[CH:23])[CH3:19]>O1CCOCC1>[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:23]#[C:22][CH:21]([O:24][CH2:25][CH3:26])[O:20][CH2:18][CH3:19])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 662853,3-DiethoxypropyneHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 21430573HCID 21430573, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Benzamidopiperidine (62 g.) was added to a stirred suspension of 1.1 g. cupric acetate and 9.5 g. paraformaldehyde in 300 ml. dry dioxane, followed by propiolaldehyde diethylacetal (38.6 g.). Stirring was continued for 24 hours at 80° C under nitrogen. The hot reaction mixture was filtered and the filtrate was evaporated. Recrystallisation ofthe solid residue from ethyl acetate-petroleum ether (bp. 60°-80° C) gave 4-benzamido-1-(4,4-diethoxybut-2-ynyl)piperidine as colourless shining leaflets. (84.6 g.), m.p. 130° C. (Found: C, 69.5; H, 8.3; N, 8.3 C20H28N2O3 requires C, 69.7; H, 8.2; N, 8.1%).

Workup

  1. filtrationThe hot reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customRecrystallisation ofthe solid residue from ethyl acetate-petroleum ether (bp. 60°-80° C)

Sources & evidence

ORD record
ord-b553204104e240e289629d5fc5a031e6
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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