Triethylamine → HCID 86620459, compound

HRID 561213Notes

Reaction equation

HRID 561213 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[N:16]#[C:17]Br.C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:17]#[N:16])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 578327574-(2-Bromo-5-fluorophenoxy)piperidine

Product 1

HCID 86620459HCID 86620459, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-bromo-5-fluorophenoxy)piperidine (2.0 g, 7.30 mmol) in THF (24.3 ml) was added cyanogen bromide (0.77 g, 7.30 mmol) followed by triethylamine (1.01 ml, 7.3 mmol) at 0° C. The mixture was warmed to rt and further stirred for 1 h. Solvent was evaporated and the residue was diluted with 1N HCl (20 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic fractions were washed with water (20 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure to afford the title compound as a solid which was used in the next step without further purification.

Workup

  1. customSolvent was evaporated
  2. additionthe residue was diluted with 1N HCl (20 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  4. washThe combined organic fractions were washed with water (20 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-681af696eefd4038a401d315f39a9be5
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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