Benzyl Bromide → HCID 10589829, compound

HRID 1955700Notes

Reaction equation

HRID 1955700 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 (2.5M, 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-1f2019a43a69408cbd9c3b7f3cea0a8b
Source dataset
uspto-grants-1998_07
Patent number
US05776959

Reaction notes

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