Potassium Carbonate → HCID 22996260, compound

HRID 1167360Notes

Reaction equation

HRID 1167360 reaction equation
[ClH:1].[NH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.C(OCC)(=O)C>[ClH:1].[NH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 22996256HCID 22996256, compound

Product 1

HCID 22996260HCID 22996260, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

4-(3-Amino-3-methylbutyl)phenol hydrochloride (1.14 g, 5.3 mmol), 4-fluorobenzonitrile (0.77 g, 6.4 mmol, 1.2 eq.) and potassium carbonate (1.65 g, 11.6 mmol, 2.2 eq.) were suspended in N,N-dimethyl-acetamide (15 ml) and stirred for 16 hours at 110° C. After this time, the darkened mixture was allowed to cool to ambient temperature. The suspension was diluted with ethyl acetate (100 ml) and washed with 1N NaOH (2×100 ml). The organic layer was treated with 5N HCl (100 ml), producing a white precipitate at the biphasic interface. The solid material was filtered and dried, triturated with pentane and dried in vacuo for 14 hours to produce a white solid (1.04 g, 71%). NMR, MS

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with 1N NaOH (2×100 ml)
  3. additionThe organic layer was treated with 5N HCl (100 ml)
  4. customproducing a white precipitate at the biphasic interface
  5. filtrationThe solid material was filtered
  6. customdried
  7. customtriturated with pentane
  8. customdried in vacuo for 14 hours

Sources & evidence

ORD record
ord-87a9b5f028634e939c5b5a3a75e10617
Source dataset
uspto-grants-2003_09
Patent number
US06617347B1

Reaction notes

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