Piperidine → HCID 86637703, compound

HRID 216007Notes

Reaction equation

HRID 216007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:15]=[N:16][N:17]([CH:19](Br)[CH2:20][CH3:21])[N:18]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][CH2:20][CH2:21][CH:25]4[CH2:26][CH2:27][CH2:28][NH:23][CH2:24]4)[N:18]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10340Sodium CarbonateHCID 86637704HCID 86637704, compound

Product 1

HCID 86637703HCID 86637703, compoundYield 131.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

41-[3-[4-(p-chlorophenyl)-5-phenyl-(-[1,2,3]triazol-2-yl)]-3-bromopropane (26 mg, 0.07 mmol) and piperidine (9 mg, 0.10 mmol) were refluxed in ethanol for 1 h in presence of dry sodium carbonate (11 mg, 0.10 mmol). The reaction mixture was then filtrated. The solid was washed with CH2Cl2. The combined filtrates was evaporated in vacuo. The resulting oil was then purified by chromatography on silica gel eluting with EtOAc to afford 1-[3-[4-(p-chlorophenyl)-5-phenyl-(-[1,2,3]triazol-2-yl)propyl]-piperidine (35 mg, 75% yield); 1H NMR (200 MHz, CDCl3, 25° C.) δ=7.53-7.46 (4H, m), 7.39-7.31 (5H, m), 4.52 (2H, t, 3J=7.1 Hz), 2.46-2.39 (6H, m), 2.23 (2H, qt, 3J=7.2 Hz), 1.58 (4H, qt, 3J=5.5 Hz), 1.42 (2H, qt, 3J=5.5 Hz) ppm. ES-MS: m/z=382 (5), 381 (4), 380 (14) [M+●]; 98 (100) [M-283]; 84 (30) [M-297].

Workup

  1. filtrationThe reaction mixture was then filtrated
  2. washThe solid was washed with CH2Cl2
  3. customThe combined filtrates was evaporated in vacuo
  4. customThe resulting oil was then purified by chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-818d882720a140e8a483065250d1459f
Source dataset
uspto-grants-2012_06
Patent number
US08193223B2

Reaction notes

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