Acetic Acid → HCID 59543436, compound
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.[C:15]1(=O)[CH2:18][CH2:17][CH2:16]1.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:15]3[CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[N:6][CH:7]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 62 °C
Procedure
1-(5-Bromopyridin-2-ylmethyl)piperazine (10 g, 39.04 mmol) was dissolved in THF (65 ml), water (0.6 mL), cyclobutanone (4.1 g, 58.6 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 heated at 62° C. for 1.5 hours (LC-MS showed full conversion). The reaction mixture was however left overnight at 62° 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 gave 7.65 g (63%) of a thick oil.
Workup
- temperatureThe reaction mixture was then heated
- extractionThe water phase was extracted with DCM (2×25 mL)
- washThe combined DCM phase was washed with water (2×25 mL), brine (2×25 mL) finally dried MgSO4
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-15faabdaa0714f189c25e97e9fb56ac4
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344001B2
Reaction notes
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