cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-yl-N,N-dimethylmethanamine;iron(2+) → HCID 178483164, compound

HRID 455943Notes

Reaction equation

HRID 455943 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH2:9][C-:8]=[CH:7][C:6]=1[CH2:10][NH:11]C1C=CN=C2C=1C=CC(Cl)=C2)[CH3:3].[CH2:23]1[C-:27]=[CH:26][CH:25]=[CH:24]1.[Fe+2:28].CN(C[C-]1C=CC=C1C=O)C.[CH-]1C=CC=C1.[Fe+2].CN(C[C-]1C=CC=C1)C.[CH-]1C=CC=C1.[Fe+2]>>[NH2:11][CH2:10][C-:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[CH2:4][N:2]([CH3:3])[CH3:1].[CH-:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1.[Fe+2:28]

Participants

4

Reactant 3

HCID 15764045cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-yl-N,N-dimethylmethanamine;iron(2+)HCID 568418013-(((7-chloroquinolin-4-yl)amino)methyl)-4-((dimethylamino)methyl)cyclopenta-1,3-dien-1-ide cyclopenta-1,3-dien-1-ide iron(II)HCID 178483165HCID 178483165, compound

Product 1

HCID 178483164HCID 178483164, compoundYield 85%

Procedure

The known method for the manufacture of ferroquine, partially represented in scheme 2 below, consists in synthesizing firstly 1-[(dimethylamino)methyl]-2-formyl-ferrocene from (dimethylamino)methyl-ferrocene with a yield of about 85%, then in preparing the corresponding intermediate oxime, and finally in carrying out reduction of this oxime which leads to obtaining 1-(aminomethyl)-2-[(dimethylamino)methyl]-ferrocene which can be isolated in the form of dihydrochloride. The yield of synthesis of the dihydrochloride 1-(aminomethyl)-2-[(dimethylamino)methyl]-ferrocene relative to 1-[(dimethylamino)methyl]-2-formyl-ferrocene is 55-65%.

Sources & evidence

ORD record
ord-4b5e27ef9e934a179090949985f2042d
Source dataset
uspto-grants-2013_07
Patent number
US08497375B2

Reaction notes

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