Iodoethane → HCID 10704698, compound

HRID 1108375Notes

Reaction equation

HRID 1108375 reaction equation
CC1[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].I[CH2:17][CH3:18].[CH:19]([N-]C(C)C)(C)[CH3:20].[Li+].CN(P(N(C)C)(N(C)C)=O)C>C1COCC1>[CH2:19]([C:17]1([CH3:18])[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]1=[O:15])[CH3:20]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 111064462-Piperidinone, 3-methyl-1-(phenylmethyl)-

Product 1

HCID 10704698HCID 10704698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction of 3-methyl-1-phenylmethyl-2-piperidinone (Meyers A I, Kunnen K B, Still W C (1987) "Conformational effects on the regiochemical metalation of C5-C13 N-benzyl lactams" J. Am. Chem. Soc., 109, 4405-4407.) (3.25 g, 16 mmol) with iodoethane (3.92 g, 25.1 mmol) in the presence of lithium diisopropylamide (prepared by treating diisopropylamine (2.42 g, 24 mmol) with butyllithium in hexanes (2.5 M, 9.2 mL, 22.9 mmol)) in THF (45 mL) and HMPA (2.4 ml,, 13.8 mmol) as described above in the preparation of Example 10, gave 5.90 g of pale yellow colored oil. Column chromatography over silica gel (hexanes-EtOAc, 9:1) afforded the product lactam (2.52 g, 68%) as a colorless viscous liquid. Analytical sample was prepared by bulb-to-bulb distillation (pot temp. 110-115° C. (1 mmHg)).

Sources & evidence

ORD record
ord-e508cb9fd237467ab303f6f34331014d
Source dataset
uspto-grants-2000_05
Patent number
US06066666

Reaction notes

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