Piperidine → HCID 69074752, compound

HRID 1727908Notes

Reaction equation

HRID 1727908 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[CH2:10][C:11]([CH2:13][O:14][CH2:15][CH2:16][Cl:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.N1CCCCC1.[C:34]([CH2:36][CH2:37][O:38][C:39](=[O:44])/[CH:40]=[C:41](\[NH2:43])/[CH3:42])#[N:35]>CC(O)C.C(O)(=O)C>[C:34]([CH2:36][CH2:37][O:38][C:39]([C:40]1[CH:23]([C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([Cl:19])[CH:21]=2)[C:10]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:18])=[C:11]([CH2:13][O:14][CH2:15][CH2:16][Cl:17])[NH:43][C:41]=1[CH3:42])=[O:44])#[N:35]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 136714102-Cyanoethyl 3-aminocrotonateHCID 22570154Phenylmethyl 4-(2-chloroethoxy)-3-oxobutanoate

Product 1

HCID 69074752HCID 69074752, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

500 mg (1.90 mmol) of 4-(2-chloroethoxy) acetoacetic acid benzyl ester, 260 mg (1.90 mmol) of 3-chlorobenzaldehyde, acetic acid and piperidine were heated and stirred at room temperature for 24 hours in 3 ml of 2-propanol. 280 mg (1.90 mmol) of 3-aminocrotonate 2-cyanoethyl ester was added and further heated and stirred at 50° C. for 48 hours. 2-propanol was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound.

Workup

  1. temperaturefurther heated
  2. custom2-propanol was evaporated under reduced pressure
  3. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-eda29b8a8bf94065acea015cd471b7c9
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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