Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.C(N=C=NC(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:31][C:32]1[CH:50]=[CH:49][C:35]([CH2:36][N:37]2[CH2:42][CH2:41][CH:40]([CH2:43][NH:44][C:45](=[O:48])[CH2:46][NH2:47])[CH2:39][CH2:38]2)=[CH:34][CH:33]=1>C(Cl)(Cl)Cl.C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:47][CH2:46][C:45]([NH:44][CH2:43][CH:40]1[CH2:41][CH2:42][N:37]([CH2:36][C:35]2[CH:49]=[CH:50][C:32]([Cl:31])=[CH:33][CH:34]=2)[CH2:38][CH2:39]1)=[O:48])=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Bromo-4-methylbenzoic acid (0.060 mmol), diisopropylcarbodiimide (0.060 mmol) and HOBt (0.060 mmol) were added to a solution of 1-(4-chlorobenzyl)-4-[(glycylamino)methyl]piperidine (0.050 mmol) in chloroform (1.35 mL) and tert-butanol (0.15 mL). The resulting reaction mixture was stirred at room temperature for 15 hours. The mixture was then loaded onto a Varian™ SCX column and washed with methanol/chloroform=1:1 (12 mL) and methanol (12 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (5 mL) and concentrated to thereby afford 4-[[N-(3-bromo-4-methylbenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine (Compd. No. 1113) (16.1 mg, 65%). The purity was determined by RPLC/MS (95%). ESI/MS m/e 494.0 (C23H27BrClN3O2).
Workup
- customThe resulting reaction mixture
- washwashed with methanol/chloroform=1:1 (12 mL) and methanol (12 mL)
- customThe obtained crude product
- washwas eluted with a 2 M methanol solution of NH3 (5 mL)
- concentrationconcentrated to thereby afford 4-[[N-(3-bromo-4-methylbenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine (Compd. No
Sources & evidence
- ORD record
- ord-fac85c040d5049d0afcd61252ffa636f
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390830B1
Linked notes
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