Water → HCID 43590388, compound

HRID 602163Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH:16]1[CH2:21][CH2:20][CH2:19][CH:18]([CH2:22][OH:23])[CH2:17]1.O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[OH:23][CH2:22][CH:18]1[CH2:19][CH2:20][CH2:21][N:16]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:17]1

Participants

Conditions

Temperature: 130 °C

Procedure

2-Fluorobenzaldehyde (3.26 mL, 30.0 mmol), potassium carbonate (5.64 g, 40.0 mmol) and tetrabutylammonium iodide (739 mg, 2.00 mmol) were added to 3-piperidylmethanol (2.30 g, 20.0 mmol) in N,N-dimethylformamide (20 mL). The reaction mixture was stirred at 130° C. for 8 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1) gave 1.56 g (36%) of the desired compound as a yellow oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialby drying over magnesium sulfate and evaporation of the solvent
customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1)

Sources & evidence

ORD record: ord-695fad0a9b2d411bb999d09e45fe424e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902367B2

Reaction notes

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