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

HRID 576472
Notes
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Reaction equation

HRID 576472 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-ef7b3a3910b1408582f57406007b65c7
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040445B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes