2-Chloroanisole → hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

HRID 848411Notes

Reaction equation

HRID 848411 reaction equation
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[CH3:16][N:17]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:24].Cl[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33]>CCCCCC.C1COCC1>[CH3:33][O:32][C:27]1[CH:26]=[C:31]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][N:17]([CH3:16])[C:18]2=[O:24])[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 130112-ChloroanisoleHCID 130352,2,6,6-TetramethylpiperidineHCID 17369N-MethylcaprolactamHCID 178418339Butyllithium2×

Product 1

HCID 2727906hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

A solution of butyl lithium (0.05 moles) in hexane (31.25 ml), was treated with 2,2,6,6-tetramethylpiperidine (8.5 ml), followed by THF (100 ml) under an inert atmosphere at 0° C. A solution of N-methylcaprolactam (6.25 ml, 50 mM) in THF (20 ml) was added, the mixture stirred for 30 minutes and treated with a solution of butyl lithium (0.05 mole) in hexane (31.25 ml). After 15 minutes, o-chloroanisole (6.2 ml) was added and the mixture stirred for fifteen hours at ambient temperature.

Workup

  1. waitAfter 15 minutes
  2. stirringthe mixture stirred for fifteen hours at ambient temperature

Sources & evidence

ORD record
ord-8e88b4b1248e459c99e854fbe4ee5c99
Source dataset
uspto-grants-1981_10
Patent number
US04296029

Reaction notes

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