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

HRID 576472Notes

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]

Participants

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

temperatureto warm to room temperature
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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