Acetic Acid → HCID 59543409, compound

HRID 1798951Notes

Reaction equation

HRID 1798951 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:6][CH:7]=1.[CH3:15][C:16](=O)[CH3:17].C(O)(=O)C.[BH3-]C#N.[Na+].[OH-].[Na+]>C1COCC1.O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH:16]([CH3:17])[CH3:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 52903243HCID 52903243, compound

Product 1

HCID 59543409HCID 59543409, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

1-(5-Bromopyridin-2-ylmethyl)piperazine (10 g, 39.04 mmol) was dissolved in THF (65 ml), water (0.6 mL), propanone (4.5 g, 78.08 mmol) and acetic acid (7.5 g, 125 mmol) was mixed. Then 1M NaCNBH3 in THF (3.68 g, 58 mmol) (58 mL) was added. The reaction mixture was then heated and 21eq. water was added in order to solve the rest of material in the mixture. The reaction mixture was stirred overnight at 45° C. The reaction mixture was added DCM (150 mL) and water (100 mL). pH was adjusted to pH=10 with 4N NaOH. The water phase was extracted with DCM (2×25 mL). The combined DCM phase was washed with water (2×25 mL), brine (2×25 mL) finally dried MgSO4, filtered and evaporated in vacuo giving 7.56 g (65%) of a thick oil.

Workup

  1. temperatureThe reaction mixture was then heated
  2. extractionThe water phase was extracted with DCM (2×25 mL)
  3. washThe combined DCM phase was washed with water (2×25 mL), brine (2×25 mL) finally dried MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4700a6419d4548e483381378eecf37b2
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

Loading…