Methylamine → 2-((Methylamino)methyl)fluorene

HRID 1844487

Reaction equation

HRID 1844487 reaction equation
C1C2CC3C(=CC=CC=3)C=2C=CC=1C(Cl)=O.CN.[CH3:19][NH:20][C:21]([C:23]1[CH:35]=[CH:34][C:33]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][C:25]=2[CH:24]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOCC>[CH3:19][NH:20][CH2:21][C:23]1[CH:35]=[CH:34][C:33]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][C:25]=2[CH:24]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 10704314N-methyl fluorene-2-carboxamideHCID 178156299H-Fluorene-2-carbonyl chlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 126897512-((Methylamino)methyl)fluorene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of fluorene-2-carbonyl chloride (prepared from fluorene-2-carboxylic acid and oxalyl chloride) in THF is added to aqueous methylamine (2 molar equivalents) to prepare N-methyl fluorene-2-carboxamide. Reduction of the amide using LiAlH4 in ether provides 2-((methylamino)methyl)fluorene. The amine is protected by reaction with di-tert-butyl dicarbonate to provide 2-((N-tBOC-N-methylamino)methyl)fluorene.

Sources & evidence

ORD record
ord-fed1647a2c5646559da749e107c1a7db
Source dataset
uspto-grants-2015_02
Patent number
US08946405B2

Linked notes

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