Malonic Acid → HCID 70435416, compound

HRID 652101Notes

Reaction equation

HRID 652101 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=2)=[N:5][C:4]([CH:25]=O)=[N:3]1.C(O)(=O)[CH2:28][C:29]([OH:31])=[O:30].N1CCCCC1>N1C=CC=CC=1>[OH2:11].[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:13]=2)=[N:5][C:4]([CH:25]=[CH:28][C:29]([OH:31])=[O:30])=[N:3]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 12774364HCID 12774364, compound

Product 1

HCID 70435416HCID 70435416, compoundYield 192.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-carboxaldehyde (0.8 g), malonic acid (0.23 g), piperidine (0.05 ml) and pyridine (5 ml) was heated at 90° for 4 h. The resulting solution was azeotroped with toluene to give a brown foam (0.9 g) which was partitioned between aqueous sodium hydroxide and diethyl ether. The aqueous layer was acidified (pH 5.5) to precipitate the title compound (0.4 g) as a white solid, m.p. 95°-100° [decomp].

Workup

  1. customThe resulting solution was azeotroped with toluene

Sources & evidence

ORD record
ord-42d11cc63ff64655834a1bd14de5b954
Source dataset
uspto-grants-1987_06
Patent number
US04670448

Reaction notes

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