Piperazine → 1-Boc-4-(2-piperazin-1-yl-benzoyl)-piperazine

HRID 1592709Notes

Reaction equation

HRID 1592709 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2Br)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 17952334Tert-butyl 4-(2-bromobenzoyl)piperazine-1-carboxylate

Product 1

HCID 694101761-Boc-4-(2-piperazin-1-yl-benzoyl)-piperazine

Procedure

Boc protected piperazine (849 mg, 4.56 mmol) was dissolved in DCM (20 mL) and triethyl amine (2.54 mL, 18.2 mmol) was added. To the stirred solution, ortho-bromo benzoyl chloride (2 g, 9.11 mmol) was added via syringe under nitrogen. The system was stirred for about 12 hours at r.t. The reaction was washed with water, dried, filtered, and concentrated. The residue was subjected to chromatography on silica gel to give 1-Boc-4-(2-bromo-)-piperazine (1.48 g, 8.85 mmol) as a white foam. 1-Boc-4-(2-bromo-benzoyl)-piperazine was coupled to piperazine in a manner similar to Preparation 1A. LRMS (ESI+): 375.2 (M+1)

Sources & evidence

ORD record
ord-9082b4a557f14a0db95363dc56e97111
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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