Dimethylformamide → 3-(1-Ethylpiperidin-4-YL)phthalonitrile

HRID 1879008Notes

Reaction equation

[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11](S(C)(=O)=O)[C:10]=2F)[CH2:5][CH2:4]1)[CH3:2].[C-:20]#[N:21].[Na+].C1OCCOCCOCCOCCOCCOC1.C[N:42]([CH3:45])C=O>>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:20]#[N:21])[C:10]=2[C:45]#[N:42])[CH2:5][CH2:4]1)[CH3:2]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 8929Sodium Cyanide

HCID 2855718-Crown-6

HCID 11701939Ordopidine

Product 1

HCID 675332423-(1-Ethylpiperidin-4-YL)phthalonitrile

Procedure

Preparation according to Example 31: 1-ethyl-4-[2-fluoro-3-(methylsulfonyl)phenyl]-piperidine (1.06 g, 3.72 mmol), N,N-dimethylformamide (30 ml), sodium cyanide (0.7 g, 14.0 mmol) and 18-crown-6-ether (5 mg). Yield: 0.35 g. MS m/z (relative intensity, 70 eV) 239 (M+, 3), 225 (17), 224 (bp), 154 (6), 71 (5).

Workup

customPreparation

Sources & evidence

ORD record: ord-ad4ab210e469424ca8534b49d0dfc928
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314126B2

Reaction notes

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