Piperidine → HCID 83151950, compound

HRID 401768Notes

Reaction equation

HRID 401768 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[ClH:13].[NH2:14][C:15]1[S:16][C:17](Cl)=[CH:18][N:19]=1.CCN(CC)CC.N1CCCCC1.[BH4-].[Na+]>C(Cl)Cl>[Cl:13][C:18]1[N:19]=[C:15]([NH:14][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=2[O:2][CH3:1])[S:16][CH:17]=1

Participants

7

Reactant 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 691752,4-DimethoxybenzaldehydeHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 83151950HCID 83151950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,4 Dimethoxybenzaldehyde (5 g, 30 mmol, 1 eq), 2-amino-5-chlorothiazole hydrochloride (5.15 g, 30 mmol, 1 eq), Et3N (3.04 g, 30 mmol, 1 eq) and piperidine (31 mg, 0.361 mmol, 0.012 eq) were combined in DCM (100 ml) and the reaction mixture heated to reflux over sieves for 18 hours. The sieves were removed by filtration and the reaction mixture diluted with MeOH (50 ml). Sodium borohydride (5.01 g, 132 mmol, 4.4 eq) was added portionwise and the reaction mixture heated to reflux for 1 hour. The mixture was cooled, quenched with water and the organic solvent evaporated in vacuo. The residue was extracted from water into ethyl acetate, dried over sodium sulphate, filtered and evaporated in vacuo. The crude material was triturated with isopropanol to yield the title compound as a cream solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux over sieves for 18 hours
  3. customThe sieves were removed by filtration
  4. additionthe reaction mixture diluted with MeOH (50 ml)
  5. temperaturethe reaction mixture heated
  6. temperatureto reflux for 1 hour
  7. temperatureThe mixture was cooled
  8. customquenched with water
  9. customthe organic solvent evaporated in vacuo
  10. extractionThe residue was extracted from water into ethyl acetate
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customThe crude material was triturated with isopropanol

Sources & evidence

ORD record
ord-cec2043a23ca4bf3a3f197eb7bd547b3
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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