Piperidine → HCID 14547436, compound

HRID 329695Notes

Reaction equation

HRID 329695 reaction equation
N1CCCCC1.[CH2:7]([O:10][CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]#[CH:9].[Cl:20][C:21]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O.[NH2:30]/[C:31](/[CH3:37])=[CH:32]\[C:33]([O:35][CH3:36])=[O:34]>C(O)(C)C>[Cl:20][C:21]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]1[C:32]([C:33]([O:35][CH3:36])=[O:34])=[C:31]([CH3:37])[NH:30][C:12]([CH2:11][O:10][CH2:7][C:8]#[CH:9])=[C:13]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 357452,3-DichlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 14271911HCID 14271911, compound

Product 1

HCID 14547436HCID 14547436, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Piperidine (2.4 g) was added dropwise over 10 minutes to a stirred mixture of ethyl 4-(prop-2-ynoxy)acetoacetate (63 g) (see Preparation 9) and 2,3-dichlorobenzaldehyde (60 g) in isopropanol (600 ml) and the mixture was stirred at room temperature for 24 hours. The mixture was then treated with methyl 3-aminocrotonate (39 g), stirred at room temperature for four days and evaporated. The residual oil was dissolved in methanol (300 ml) and the solution kept at -20° for two days. The resulting solid was collected, washed with cold methanol and dried to give the title compound (29.5 g), m.p. 104°-105°, which was used directly.

Workup

  1. stirringstirred at room temperature for four days
  2. customevaporated
  3. dissolutionThe residual oil was dissolved in methanol (300 ml)
  4. waitthe solution kept at -20° for two days
  5. customThe resulting solid was collected
  6. washwashed with cold methanol
  7. customdried

Sources & evidence

ORD record
ord-121b262495fe431186b463ed73f3bb2c
Source dataset
uspto-grants-1990_01
Patent number
US04892881

Reaction notes

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