Iodoethane → HCID 10704698, compound

HRID 1955699Notes

Reaction equation

HRID 1955699 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 (2.5M, 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-d93e7f378e0b4f0cb6a73c212b12738d
Source dataset
uspto-grants-1998_07
Patent number
US05776959

Reaction notes

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