Sodium Cyanide → HCID 18700071, compound

HRID 2289310Notes

Reaction equation

HRID 2289310 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([CH2:19]Br)=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:27]#[N:28].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([CH2:19][C:27]#[N:28])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 18700084HCID 18700084, compound

Product 1

HCID 18700071HCID 18700071, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-2-trifluoromethylbenzyl bromide (0.37 g, 0.87 mmol) from Step 4 above in DMF (4 mL) was added NaCN (0.064 g, 1.3 mmol). The mixture was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (2×25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-trifluoromethylphenylacetonitrile was a pale yellow gum (HPLC retention time=11.4 min (method A)).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (2×25 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-45c10cf34d6c45dc99571ccfb64da4ed
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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