Potassium Hydroxide → HCID 11276773, compound

HRID 1059695Notes

Reaction equation

HRID 1059695 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17]C(=O)C(F)(F)F)[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18630938HCID 18630938, compound

Product 1

HCID 11276773HCID 11276773, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-{3-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-2,2,2-trifluoroacetamide (1.77 g, 5.10 mmol) and 20% aqueous KOH (25 mL) in ethanol (50 mL) were stirred at room temperature for 30 minutes. The reaction mixture was concentrated to dryness and the solids were washed with methylene chloride, dried over magnesium sulfate and concentrated to give 3-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propylamine (0.82 g, 64%) as a waxy white solid. Mp. 57-58° C.; NMR CDCl3 δ 7.29-7.20 (m, 4H), 6.03 (s, 1H), 3.12 (d, J=3.3 Hz, 2H), 2.76 (t, J=6.9 Hz, 2H), 2.67 (t, J=5.6 Hz, 2H), 2.51-2.44 (m, 4H), 1.69 (p, J=7.5 Hz, 2H), 1.63 (s, 2H); 13C NMR CDCl3 δ 139.20, 133.96, 132.61, 128.36, 126.15, 122.41, 56.20, 53.36, 50.30, 40.77, 30.73, 28.01; IR(KBr) 2929, 2861, 2805, 2767, 2734, 1493, 1467, 1379, 1320, 1128, 1095, 845, 825, 800; Analysis calculated for C14H19CIN2.0.25H2O: C, 65.87; H, 7.70; N, 10.97. Found: C, 65.69; H, 7.44; N, 10.91.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. washthe solids were washed with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4d1c9290411140e094453b77383fb627
Source dataset
uspto-grants-2003_02
Patent number
US06521630B1

Reaction notes

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