1,2-Dichloroethane → HCID 23138332, compound
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[CH:15][CH2:16][NH:17]C(=O)OC(C)(C)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:43]CCCl>>[ClH:43].[ClH:43].[ClH:43].[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
To a solution of 1-benzylpiperazine (4.4 g), tert-butyl N-(2-oxoethyl)carbamate (3.8 g) and acetic acid (1.7 ml) in 1,2-dichloroethane (50 ml) was added sodium triacetoxyborohydride (8.1 g) under ice-cooling. The reaction mixture was mixed at room temperature for 2 days. Then, the reaction solution washed with an aqueous potassium carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was dissolved in methanol (50 ml). A 4 N solution of hydrogen chloride in ethanol (40 ml) was added thereto, and mixed at room temperature for 5 hours. The precipitate was collected by filtration and washed with diethyl ether and hexane to obtain the title compound (5.0 g, 61%).
Workup
- temperaturecooling
- additionThe reaction mixture was mixed at room temperature for 2 days
- washThen, the reaction solution washed with an aqueous potassium carbonate solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- dissolutionthe residue was dissolved in methanol (50 ml)
- additionA 4 N solution of hydrogen chloride in ethanol (40 ml) was added
- additionmixed at room temperature for 5 hours
- filtrationThe precipitate was collected by filtration
- washwashed with diethyl ether and hexane
Sources & evidence
- ORD record
- ord-c18924fa5cb045acac8b0e78eee5e729
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820673B2
Reaction notes
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