Piperidine → HCID 131715477, compound

HRID 569593Notes

Reaction equation

HRID 569593 reaction equation
N1CCCCC1.[CH3:7][C:8]1([CH3:24])[O:12][CH:11]([CH2:13][O:14][CH2:15][C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10][O:9]1.[Cl:25][C:26]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O>CC(O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][C:16]([C:15](=[CH:28][C:27]1[CH:30]=[CH:31][CH:32]=[C:33]([Cl:34])[C:26]=1[Cl:25])[O:14][CH2:13][CH:11]1[CH2:10][O:9][C:8]([CH3:7])([CH3:24])[O:12]1)=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 357452,3-DichlorobenzaldehydeHCID 198712884-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-oxo-butyric acid ethyl ester

Product 1

HCID 131715477HCID 131715477, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Piperidine (1.0 g) was added dropwise over 5 minutes to a stirred, ice-cooled solution of ethyl 4-{(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy }acetoacetate (26.0 g) (see Preparation 5) and 2,3-dichlorobenzaldehyde (17.5 g) in 2-propanol (200 ml) and the mixture was stirred with ice-cooling for 2 hours and at room temperature for 14 hours. The mixture was evaporated and the residue twice taken up in toluene and evaporated. The residue was purified by chromatography on silica (150 g) using toluene plus 0-40% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated to give essentially pure ethyl -(2,3-dichlorobenzylidene)-4-{(2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}acetoacetate (17.3 g) as an oil. A solution of this oil in 2-propanol (150 ml) was treated with methyl 3-amino-crotonate (5.0 g) and the mixture stirred at room temperature for 24 hours. The mixture was evaporated and the residue twice taken up in toluene and evaporated. The residue was purified by chromatography on SiO2 (110 g) using toluene plus 0-10% ethyl acetate as the eluant. Appropriate fractions were combined and evaporated to give the title compound (2.75 g), m.p. 135°-137° C.

Workup

  1. customThe mixture was evaporated
  2. customevaporated
  3. customThe residue was purified by chromatography on silica (150 g)
  4. customevaporated

Sources & evidence

ORD record
ord-08773dda727c405590543bf67fa34cdb
Source dataset
uspto-grants-1988_03
Patent number
US04732985

Reaction notes

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