Reaction equation
[C-:1]1([CH:6]=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13].[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].[BH4-].[Na+].C(O)(=O)C>CN(C=O)C.[OH-].[Na+].O>[C-:1]1([CH2:6][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:2]=[CH:3][CH:4]=[CH:5]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13]Participants
Conditions
- Temperature
- 80 °C
Procedure
After 1.38 g (6.4 mmol) of ferrocene-aldehyde (Aldrich Corp) was dissolved in 20 mL of a DMF solution, the mixture was mixed with a solution of 0.75 g (5.7 mmol) of 6-amino caproic acid (Merck Corp.) in 5 mL of NaOH and refluxed at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, and a solution of NaBH4 (0.63 g, 16.5 mmol) in 5 mL of water was added little by little into the reaction mixture (refer to FIG. 11). After 12 hours later, an aqueous acetic acid solution (10%) was slowly added until the pH reached 5. The reaction by-product ferrocene-CH2OH and unreacted 6-amino caproic acid dissolved in the organic phase was removed through extraction using ethylacetate. The aqueous phase was distilled at 50° C. under reduced pressure to obtain yellowish brown crystals. The yellowish brown crystals were recrystallized by dissolving the crystals in high-temperature ethanol to obtain planar, yellow crystalline N-(ferrocenyl methyl)-6-amino caproic acid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customwas removed through extraction
- distillationThe aqueous phase was distilled at 50° C. under reduced pressure
- customto obtain yellowish brown crystals
- customThe yellowish brown crystals were recrystallized
- dissolutionby dissolving the crystals in high-temperature ethanol
Sources & evidence
- ORD record
- ord-c2e5a198e4eb4adda1d5c178e958d27f
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07479254B2
Linked notes
Loading…