Diisopropylcarbodiimide → 4-[[N-(3-bromo-4-methylbenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine

HRID 1281007

Reaction equation

HRID 1281007 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:18])[CH2:16][NH2:17])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Br:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25](O)=[O:26].C(N=C=NC(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl.C(O)(C)(C)C>[Br:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25]([NH:17][CH2:16][C:15]([NH:14][CH2:13][CH:10]1[CH2:9][CH2:8][N:7]([CH2:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:12][CH2:11]1)=[O:18])=[O:26]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 821303-Bromo-4-methylbenzoic acidHCID 184261551-(4-Chlorobenzyl)-4-((glycylamino)methyl}piperidine

Product 1

HCID 184262374-[[N-(3-bromo-4-methylbenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 1-(4-chlorobenzyl)-4-{(glycylamino)methyl)piperidine (0.050 mmol) in CHCl3 (1.35 mL) and tert-butanol (0.15 mL) was treated with 3-bromo-4-methylbenzoic acid (0.060 mmol), diisopropylcarbodiimide (0.060 mmol), and HOBt (0.060 mmol). The reaction mixture was stirred at room temperature for 15 h. The mixture was loaded onto Varian™ SCX column, and washed with CH3OH/CHCl3 1:1 (12 mL) and CH3OH (12 mL). Product was eluted off using 2 N NH3 in CH3OH (5 mL) and concentrated to afford 4-[{N-(3-bromo-4-methylbenzoyl)glycyl}aminomethyl]-1-(4-chlorobenzyl)piperidine (Compound No. 1113) (16.1 mg, 65%): The purity was determined by RPLC/MS (95%); ESI/MS m/e 494.0 (C23H27BrClN3O2).

Workup

  1. washwashed with CH3OH/CHCl3 1:1 (12 mL) and CH3OH (12 mL)
  2. washProduct was eluted off
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9ed96c40a20c423e96ea478b1b68b1e3
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Linked notes

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