Piperidine → 1-(1,3-Benzoxazol-6-ylcarbonyl)-piperidine

HRID 442643Notes

Reaction equation

HRID 442643 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(C1NC=CN=1)(C1NC=CN=1)=O>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[C:7]([C:10]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 222459381,3-Benzoxazole-6-carboxylic acid

Product 1

HCID 155461431-(1,3-Benzoxazol-6-ylcarbonyl)-piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The amide is prepared by coupling 1,3-benzoxazol-6-carboxylic acid with piperidine by activation of the acid with carbonyl diimidazole as described for the preparation of Invention Compound V. Dilution of the reaction solution with more CH2Cl2 causes the product to precipitate. Purification is achieved by chromatography on silica gel. EMIS m/z=230 (parent), 229, 146 (base), and 118. 1H NMR δ 1.55 (br m, 4), 1.70 (br, 2), 3.4 (br, 2), 3.75 (br, 2), 7.48 (dd, 1, J=8.29, 1.22 Hz), 7.62 (d, 1, J=8.44 Hz), 7.84 (d, 1, J=1.00 Hz), and 8.15 ppm (s, 1).

Workup

  1. customto precipitate
  2. customPurification

Sources & evidence

ORD record
ord-078bf833a35842e59ac0f66a34470887
Source dataset
uspto-grants-1999_04
Patent number
US05891876

Reaction notes

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