Benzyl Bromide → HCID 10589829, compound

HRID 1108377Notes

Reaction equation

HRID 1108377 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([N-]C(C)C)(C)C.[Li+].CN(P(N(C)C)(N(C)C)=O)C>C1COCC1>[CH3:1][C:2]1([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 111064462-Piperidinone, 3-methyl-1-(phenylmethyl)-

Product 1

HCID 10589829HCID 10589829, compoundYield 166.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction of 3-methyl-1-phenylmethyl-2-piperidinone (3.65 g, 18 mmol) with benzyl bromide (4.84 g, 28.3 mmol) in the presence of lithium diisopropylamide (prepared by treating diisopropylamine (2.73 g, 27 mmol) with butyllithium in hexanes (2.5 M, 10.3 mL, 25.7 mmol)) in THF (45 mL) and HMPA (2.7 mL, 15.5 mmol) as described above in the preparation of Example 10, gave 8.80 g of pale yellow colored oil. Column chromatography over silica gel (hexanes-EtOAc, 9:1) afforded the product lactam (3.72 g, 71%) as a colorless viscous residue. Analytical sample was prepared by bulb-to-bulb distillation (pot temp. 150-155° C. (1.3 mmHg)).

Workup

  1. customas described above in the preparation of Example 10

Sources & evidence

ORD record
ord-a0cbb4ec79f241dbbeeb416f39b78069
Source dataset
uspto-grants-2000_05
Patent number
US06066666

Reaction notes

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