Triphenylphosphine → 4-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine

HRID 1675146

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.[CH3:28][N:29]1[C:33]([CH2:34][CH2:35]O)=[CH:32][CH:31]=[N:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:28][N:29]1[C:33]([CH2:34][CH2:35][O:27][C:24]2[CH:23]=[CH:22][C:21]([CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[CH:26][CH:25]=2)=[CH:32][CH:31]=[N:30]1

Participants

Conditions

Temperature: 22 °C

Procedure

DIAD (64.8 μl, 0.33 mmol) was added to 4-(piperidin-4-yl)phenol (CAS 263139-27-1, 53 mg, 0.30 mmol), 2-(1-methyl-1H-pyrazol-5-yl)ethanol (obtained as described in PCT Int. Appl. WO 2007017222, Intermediate 1) (37.7 mg, 0.30 mmol) and triphenylphosphine (86 mg, 0.33 mmol) in DCM (3 mL) at 20° C. under nitrogen. The resulting mixture was stirred at 22° C. for 3 days. The reaction mixture was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness to afford 4-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine (85 mg, 96%) as a yellow oil.

Workup

customThe reaction mixture was purified by ion exchange chromatography
washThe desired product was eluted from the column
customwere evaporated to dryness

Sources & evidence

ORD record: ord-64bc66898c944875a16910785de0ea9b
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Linked notes

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