Hydrochloric Acid → 2-(Methylsulfonyl)-6-(1-propylpiperidin-4-YL)benzonitrile

HRID 1878956Notes

Reaction equation

HRID 1878956 reaction equation
F[C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]1.[C-:21]#[N:22].[Na+].C1OCCOCCOCCOCCOCCOC1.Cl>CN(C)C=O>[CH3:11][S:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)[C:2]=1[C:21]#[N:22])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 2855718-Crown-6HCID 115149334-[2-Fluoro-3-(methylsulfonyl)phenyl]-1-propylpiperidine

Product 1

HCID 115440372-(Methylsulfonyl)-6-(1-propylpiperidin-4-YL)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation according to Example 7: 4-[2-fluoro-3-(methylsulfonyl)phenyl]-1-propylpiperidine (0.2 g, 0.67 mmol), N,N-dimethylformamide (30 ml), sodium cyanide (0.82 g, 1.67 mmol) and 18-crown-6-ether (5 mg). Yield: 0.06 g (29%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: MS m/z (relative intensity, 70 eV) 306 (M+, 3), 279 (6), 278 (16), 277 (bp), 198 (5).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-69f47f5310dd45dfae90c792efe8537c
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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