Hydrochloric Acid → LS-104

HRID 1818050Notes

Reaction equation

HRID 1818050 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:5]=[CH:6][CH:7]=O.[C:13]([CH2:15][C:16]([N-:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])#[N:14].N1CCCCC1.Cl>C(O)C.O>[CH2:19]([NH:18][C:16](/[C:15](=[CH:7]/[CH:6]=[CH:5]/[C:4]1[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([OH:1])[CH:3]=1)/[C:13]#[N:14])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4430343-(3,4-Dihydroxy-phenyl)-2-propenalHCID 178511179N-(cyanoacetyl)benzylamide

Product 1

HCID 9861871LS-104Yield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 3,4-dihydroxycinnamaldehyde A12 (example 59) (32 mg, 0.2 mmol) and amide A3 (Example 4) (32 mg, 0.2 mmol) in 8 mL of ethanol 40 μl of piperidine was added and the mixture was kept at room temperature for 1 h. 2N HCl and water were added and the precipitated solid was recrystallized from ethanol-water to give 44 mg (68%) of an orange solid. The analytical data were identical to the compound prepared as described in Example 8.

Workup

  1. customthe precipitated solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-786fe6528f3b4d7cb2f7f1c74206825d
Source dataset
uspto-grants-2009_10
Patent number
US07598419B2

Reaction notes

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