Piperidine → HCID 66665852, compound

HRID 406240Notes

Reaction equation

HRID 406240 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]1([C:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1CCCCC1>>[C:10]1([C:16]2[C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:8][C:7]3[C:2](=[N:3][CH:4]=[CH:5][CH:6]=3)[N:1]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 99482-PhenylacetophenoneHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 66665852HCID 66665852, compound

Conditions

Temperature
120 °C

Procedure

A suspension comprising 2-amino-pyridine-3-carbaldehyde (5 g, 40.9 mmol) and deoxybenzoin (8.03 g, 40.9 mmol) in piperidine (4.46 ml, 45.0 mmol) was heated at 120° C. overnight. The resulting solution was partitioned between DCM (200 ml) and water (200 ml). The organic layer was separated and washed with water (2×150 ml), brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title product as a yellow solid;

Workup

  1. customThe resulting solution was partitioned between DCM (200 ml) and water (200 ml)
  2. customThe organic layer was separated
  3. washwashed with water (2×150 ml), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-5d16442310f842fc85449c6dd3123f35
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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