Sodium Cyanide → HCID 11543903, compound

HRID 1878948Notes

Reaction equation

HRID 1878948 reaction equation
F[C:2]1[C:7]([C:8]([F:11])([F:10])[F: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.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:18]([N:15]1[CH2:16][CH2:17][CH:12]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]=2[C:21]#[N:22])[CH2:13][CH2:14]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 10340Sodium CarbonateHCID 2855718-Crown-6HCID 11565504HCID 11565504, compound

Product 1

HCID 11543903HCID 11543903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-fluoro-3-(trifluoromethyl)phenyl]-1-propylpiperidine (1.57 g, 5.4 mmol) in N,N-dimethylformamide (35 ml) was added sodium cyanide (1.0 g, 20 mmol) and 18-crown-6-ether (50 mg). The mixture was heated at reflux for 15 h and then brought to ambient temperature. Aqueous sodium carbonate (10%, 50 ml) was added and the phases were separated. The aqueous phase was extracted with ethylacetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. Purification by flash column chromatography (ethylacetate/methanol, 1:1) gave the title compound: 0.72 g (45%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 272-274° C. MS m/z (relative intensity, 70 eV) 296 (M+, 4), 268 (16), 267 (bp),204 (3), 184 (3).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 h
  3. custombrought to ambient temperature
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with ethylacetate (2×50 ml)
  6. dry with materialthe combined organic phases was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto give an oil
  9. customPurification by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record
ord-d1b0b9eb0f954762a78caafdf6386d7d
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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