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

HRID 1724099Notes

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

Reaction notes

Loading…