4-Phenylpiperidine → HCID 19367102, compound

HRID 1416290Notes

Reaction equation

HRID 1416290 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[C:13]1([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:22]3[CH2:23][CH2:24][CH:19]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:20][CH2:21]3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 698734-PhenylpiperidineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 19367102HCID 19367102, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure of Example 39, Step 2 and making non-critical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, Step 1; 0.307 g), 4-phenylpiperidine (Aldrich or Chart J; 0.2955 g), and THF (2 mL) are converted to product, which is chromatographed on silica gel using methanol/dichlormethane (4/96), followed by crystallization from ethyl acetate, to give 0.169 g of the title compound; mp 132-133° C.; MS m/z 325; IR (mineral oil) 1073, 801, 696, 1324, 1501 cm-1 ; 1H NMR (CDCl3) δ1.83, 2.20, 2.51, 3.14, 3.75, 7.11, 7.24, 7.52, 7.54, 8.13.

Workup

  1. customis chromatographed on silica gel
  2. customfollowed by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-db5c642a0c8b40a6ab85191519c60db4
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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