p-Toluenesulfonic acid → 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

HRID 749471Notes

Reaction equation

HRID 749471 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][CH:18]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[CH3:35])[CH2:19][CH2:20][O:21]C2CCCCO2)[CH3:16])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+].C(Cl)Cl>CO>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][CH:18]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[CH3:35])[CH2:19][CH2:20][OH:21])[CH3:16])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 68976383HCID 68976383, compound

Product 1

HCID 689767833-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide (460 mg, 0.96 mmol) was dissolved in methanol (10 mL) together with 4-toluenesulfonic acid (37 mg, 0.2 mmol) and the solution was stirred at room temperature overnight. An aqueous solution of NaHCO3 together with CH2Cl2 was added and the organic solution was then washed with brine, dried and the solvent removed by evaporation. There was obtained 350 mg (92%) of 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide as an oil. 1H NMR (300 MHz, CDCl3): 1.0-2.3 (cm, 6H), 2.4 (s, 3H), 2.6 (s, 3H), 2.7-4.5 (cm, 10H), 6.4-7.4 (cm, 5H).

Workup

  1. washthe organic solution was then washed with brine
  2. customdried
  3. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-5ec9093704b64f309261fc4a4c8099ce
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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