(1-Bromoethyl)benzene → HCID 19599742, compound

HRID 609656Notes

Reaction equation

HRID 609656 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19]>CN(C=O)C>[C:20]1([CH:18]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]2=[O:14])[CH3:19])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 19599742HCID 19599742, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the same way as that described in Example 1, Step 1, using Intermediate 1 (500 mg, 2.5 mmol), sodium hydride (110 mg of a 60% dispersion in mineral oil, 2.8 mmol), (1-bromoethyl)benzene (0.44 mL, 3.25 mmol) and DMF (12 mL). The title piperazinone (677 mg, 89%) was isolated as a colourless oil, which solidified on standing at 0° C. mp. 62-64° C. 1H NMR (250 MHz, CDCl3) δ1.40 (9H, s), 1.53 (3H, d, J=7.2 Hz), 2.80-2.90 (1H, m), 3.14-3.36 (2H, m), 3.56-3.71 (1H, m), 4.07 (1H, d, J=18.2 Hz), 4.22 (1H, d, 18.2 Hz), 6.08 (1H, q, J=7.2 Hz), 7.28-7.39 (5H, m).

Sources & evidence

ORD record
ord-d195f16f6f474579909b23fbfc0eb198
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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