Piperidin-4-ol → HCID 46916505, compound

HRID 2045940Notes

Reaction equation

HRID 2045940 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4].[OH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(O)(C)C>[OH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[CH:21]=[N:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH:7]=2)=[O:4])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 46916455HCID 46916455, compound

Product 1

HCID 46916505HCID 46916505, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (93 mg, 0.272 mmol) and 4-hydroxypiperidine (138 mg, 1.35 mmol) in isopropanol (5 mL) was heated at reflux for 1 h. The solvent was evaporated in vacuo and the crude reaction mixture was purified by preparative LCMS to afford 2-(4-hydroxypiperidin-1-yl)-N-(3-(quinoxalin-2-yl)phenyl)acetamide (26 mg, 26% yield). LCMS calculated for C21H22N4O2 (M+H): 363.43. found 363.40. 1H-NMR (CD3CN, 400 Mhz) δH: 9.55 (1H, br.), 9.25 (1H, s), 8.40 (1H, m), 8.00-8.05 (2H, m), 7.85-7.90 (1H, m), 7.65-7.80 (3H, m), 7.40-7.48 (1H, m), 3.65 (1H, m), 3.22 (2H, s), 2.85-3.15 (OH and 2H, br. and m), 2.40-2.50 (2H, m), 1.82-1.92 (2H, m), 1.55-1.68 (2H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customThe solvent was evaporated in vacuo
  4. customthe crude reaction mixture
  5. customwas purified by preparative LCMS

Sources & evidence

ORD record
ord-2678c8498ee94f8b9f3ed68986f0ba88
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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