N-Didesmethyl Loperamide synthesis

4synthesis methods

Product Name:N-Didesmethyl Loperamide
CAS Number:66164-06-5
Molecular formula:C27H29ClN2O2
Molecular Weight:448.98

63959-33-1 Synthesis

4-(4-Chlorophenyl)-4-hydroxy-a,a-diphenyl-1-piperidinebutanenitrile

63959-33-1
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66164-06-5
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Yield:66164-06-5 87%

Reaction Conditions:

with potassium hydroxide in tert-butyl alcohol at 100; for 72 h;Inert atmosphere;

Steps:

4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-2,2-diphenylbutanamide (b)

4-(4-Chlorophenyl)-4hydroxypiperidin-1-yl)-2,2- diphenylbutanenitrile (1.5 g, 3.5 mmol) was dissolved in ^tbutanol (10 mL) and potassium hydroxide (589.15 mg, 10.5 mmol) was added. The reaction mixture was stirred at 100°C for 3 days. After concentration under vacuum, the crude material was re-dissolved in dichloromethane and filtered through a pad of celite. After evaporate the organic solvent, the residue was purified on silica gel column eluted with MeOH: CH₂Cl₂ (5:95 v/v) to give 1.37 mg (3.05 mmol, 87% yield) compound b as a white solid. TLC (silica gel; MeOH: CH₂Cl₂ (5:95 v/v)); R_f=0.2. ¹H NMR (CDCl₃): δ 7.39 (d, J=4.8Hz, 2H), 7.29 (m, 12H), 6.56 (s, 1H), 5.58 (s, 1H), 2.79 (d, J=11.37 Hz, 2H), 2.67(t, J=7.67 Hz, 2H), 2.44 (m, 4H), 2.09 (t, J=12.64 Hz, 2H), 1.70 (d, J=11.91 Hz, 2H). ¹³C NMR (CDCl₃): δ 175.89, 145.92, 142.45, 132.03, 127.92, 127.65, 126.31, 125.37, 69.96, 59.11, 54.16, 48.70, 37.31, 34.91. LC- MS, [M+H]⁺, 449.3, Calculated for C₂₇H₃₀ClN₂O₂ [M⁺+H], 449.1990.