Triphenylphosphine → HCID 14837039, compound

HRID 2072802Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[C:21](O)=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:17]=1[F:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:21]2[C:20]([F:23])=[C:19]([F:24])[C:18]([F:25])=[C:17]([F:26])[C:16]=2[F:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A stirred mixture of 10.33 g of 1-benzyl-4-hydroxy piperidine, 9.93 g of pentafluorophenol, and 15.58 g of triphenylphosphine in 200 ml of benzene was cooled to 10° C. At this temperature, a solution of 10.35 g of diethyl azodicarboxylate in 50 ml of benzene was added, dropwise, over one hour. After stirring for 20 hours at ambient temperature, the reaction mixture was filtered and concentrated to an oil. The oil was purified by means of high pressure liquid chromatography (silica gel; elution with ethylacetate/dichloromethane 1:1). Evaporation of the appropriate fractions afforded 14.5 g of 1-benzyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil. Conversion of the free base to the corresponding hydrochloride salt afforded 8.2 g (42%) of 1-benzyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine hydrochloride, m.p. 244°-246° C.

Workup

filtrationthe reaction mixture was filtered
concentrationconcentrated to an oil
customThe oil was purified by means of high pressure liquid chromatography (silica gel; elution with ethylacetate/dichloromethane 1:1)
customEvaporation of the appropriate fractions

Sources & evidence

ORD record: ord-40105a02be2344b1b6826513dec6f725
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04914204

Reaction notes

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