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1-Iodo-N,N-dimethylmethanamine → 1,2-Bis(dimethylaminomethyl)ferrocene

HRID 1724099
Notes
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Reaction equation

HRID 1724099 reaction equation
C([Li])CCC.[CH3:6][N:7]([CH2:9][C-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[CH3:8].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20].I[CH2:22][N:23]([CH3:25])[CH3:24]>C(OCC)C>[CH3:6][N:7]([CH2:9][C-:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:22][N:23]([CH3:25])[CH3:24])[CH3:8].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 111713991-Iodo-N,N-dimethylmethanamineHCID 15764045cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-yl-N,N-dimethylmethanamine;iron(2+)HCID 178418339Butyllithium

Product 1

HCID 1317272661,2-Bis(dimethylaminomethyl)ferrocene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

n-Butyllithium (Aldrich, 2.5 molar in hexane, 24 ml, 54 mmol) is added to a solution of (dimethylaminomethyl)ferrocene (Aldrich, 13.13 g, 10.69 ml, 48.97 mmol) in diethyl ether (80 ml) under nitrogen at a temperature of 25° C. and the reaction mixture stirred for 4 hours. The resulting red solution is then cooled to approximately −70° C. in a dry ice/acetone bath and Eschenmosers salt (ICH2NMe2)(Aldrich, 10 g, 54 mmol) is added. The reaction is allowed to warm to room temperature and stirred overnight.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight

Sources & evidence

ORD record
ord-45aeb3745a0c4556a66610a45ce55692
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07485739B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes