2,4-Difluorobenzaldehyde → n-(2,4-Difluorophenylmethyl)-n-[dimethyl(t-butyldimethylsiloxymethyl)methyl]amine

HRID 636743Notes

Reaction equation

[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[O:11]([CH2:19][C:20]([NH2:23])([CH3:22])[CH3:21])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:23][C:20]([CH3:22])([CH3:21])[CH2:19][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,4-difluorobenzaldehyde (1.42 g, 10.0 mmol) in toluene (30 ml) was added 1-t-butyldimethylsiloxy-2-methyl-2-propylamine (2.03 g, 10.0 mmol) and stirred under reflux using a Dean-Stark trap to remove water for 6 hours. The solvent was evaporated and the residue was dissolved in methanol (10 ml). The solution was cooled to 0° C. in ice-water bath and an excess amount of NaBH4 was added. The mixture was gradually warmed to room temperature and stirring was continued until the Schiff base disappeared. The mixture was added to 1N NaOH aqueous solution, extracted with toluene, washed with sat. NaCl aqueous solution and dried over MgSO4. The solvent was evaporated to give the crude title compound (2.92 g; 92% in 2 steps).

Workup

temperatureunder reflux
customto remove water for 6 hours
customThe solvent was evaporated
dissolutionthe residue was dissolved in methanol (10 ml)
additionan excess amount of NaBH4 was added
temperatureThe mixture was gradually warmed to room temperature
stirringstirring
additionThe mixture was added to 1N NaOH aqueous solution
extractionextracted with toluene
washwashed with sat. NaCl aqueous solution
dry with materialdried over MgSO4
customThe solvent was evaporated

Sources & evidence

ORD record: ord-780071aa4aef4ec6ac9f65041a14ea17
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194461B1

Reaction notes

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