1-Piperidinecarboxaldehyde → HCID 22387817, compound

HRID 1699909Notes

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-d6854a06993745948fc43af6b4ad34e8
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348474B1

Reaction notes

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