Sodium Cyanide → HCID 19065051, compound

HRID 482020Notes

Reaction equation

HRID 482020 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[C-]#[N:14].[Na+].C(OC([N:26]1[CH2:31][CH2:30][CH:29]([C:32](=O)[CH:33]=[CH:34][C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[CH2:28][CH2:27]1)=O)C1C=CC=CC=1>CN(C=O)C>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([C:6]2[NH:14][C:32]([CH:29]3[CH2:28][CH2:27][NH:26][CH2:31][CH2:30]3)=[CH:33][C:34]=2[C:35]2[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 679903-(Trifluoromethyl)benzaldehydeHCID 53832831HCID 53832831, compound

Product 1

HCID 19065051HCID 19065051, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To m-trifluoromethylbenzaldehyde (2.44 g, 0.014 mol) in 5 mL of DMF was added NaCN (0.147 g, 0.003 mol) and the mixture was stirred under argon for 1 hour. This solution was added to 1-(1-benzyloxycarbonyl-4-piperidinyl)-3-(4-pyridyl)-2-propen-1-one in 10 mL of DMF. The mixture was stirred at 65°-75° C. for 20 hours. The volatile components were removed in vacuo. The residual oil was taken up in EtOAc and sat'd NaCl. The EtOAc extract was separated, dried, filtered and concentrated in vacuo to form an oil. The crude oil was chromatographed on silica gel eluting with ethyl acetate, producing 3.45 g of the title compound as a yellow foam.

Workup

  1. stirringThe mixture was stirred at 65°-75° C. for 20 hours
  2. customThe volatile components were removed in vacuo
  3. extractionThe EtOAc extract
  4. customwas separated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto form an oil
  9. customThe crude oil was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-e87ec4de84764c5599b069a4bc072e48
Source dataset
uspto-grants-1998_08
Patent number
US05792778

Reaction notes

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