Acetic Acid → 1-(4-Bromophenyl)-4-methylpiperazine
Reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C=O.[CH3:17]C(O)=O.[BH4-].[Na+].[NH4+].[Cl-]>C(Cl)Cl.CO>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:17])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1-(4-bromophenyl)piperazine hydrochloride (1.0 g, 3.61 mmol), formaldehyde (37% aqueous, 3 mL, 39.71 mmol), AcOH (0.23 mL, 3.97 mmol) and MeOH (30 mL) was heated at 80° C. under nitrogen. After 1.5 hours, the mixture was cooled to 0° C. in an ice bath. Methylene chloride (5 mL) was added followed by a slow addition of sodium borohydride (1.91 g, 50.54 mmol) under nitrogen. The mixture was stirred for 1 hour and then poured into a seperatory funnel containing a saturated solution of NH4Cl (25 mL) and CH2Cl2 (50 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The extracts were dried (Na2SO4), filtered and concentrated to to give the sub-title compound (900 mg, 97%) which was used without further purification.
Workup
- temperaturethe mixture was cooled to 0° C. in an ice bath
- additionpoured into a seperatory funnel
- customThe layers were separated
- extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
- dry with materialThe extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-25faed18ce264f8ea9d8e6eb50cfa2ac
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324264B1
Reaction notes
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