1-Piperidinecarboxaldehyde → HCID 22387817, compound

HRID 1072889Notes

Reaction equation

C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[C:15]([Cl:28])[CH:14]=1.[CH:29](N1CCCCC1)=[O:30].[Cl-].[NH4+]>O1CCCC1>[Si:21]([O:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH:29]=[O:30])=[CH:14][C:15]=1[Cl:28])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution (1.6 M, 8.3 ml) of n-butyl lithium/hexane was added to a solution of 4-bromo-1-((tert-butyldimethylsilyloxy)methyl)-2-chlorobenzene (4.03 g) in tetrahydrofuran (10 ml) under a nitrogen atmosphere at −60° C. and the mixture was stirred for 45 min. The reaction mixture was once heated to 0° C. and then cooled to −40° C. and 1-formyl piperidine (1.63 g) was dropwise added over 3 min. Then, the reaction mixture was heated to 0° C. over 2 hr. Aqueous ammonium chloride was added to the reaction mixture and the resulting product was extracted twice with hexane. The organic layers were combined, washed successively with diluted hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=30/1) to give the objective compound (2.49 g) as a colorless oil.

Workup

temperaturecooled to −40° C.
temperatureThen, the reaction mixture was heated to 0° C. over 2 hr
extractionthe resulting product was extracted twice with hexane
washwashed successively with diluted hydrochloric acid
dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-9e086a5c5df04214ad6516140f4432bf
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911469B2

Reaction notes

Loading…