N-Methylcaprolactam → hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

HRID 848417Notes

Reaction equation

HRID 848417 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:9].C1([Si](C2C=CC=CC=2)(C2C=CC=CC=2)[O:17][C:18]2[C:19]#[C:20][CH:21]=[CH:22][CH:23]=2)C=CC=CC=1>>[OH:17][C:18]1[CH:23]=[C:22]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][N:2]([CH3:1])[C:3]2=[O:9])[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 17369N-MethylcaprolactamHCID 20565338m-Triphenylsiloxybenzyne

Product 1

HCID 11746121hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

Procedure

Following the procedure of Example 3, reaction of the lithium anion of N-methylcaprolactam with m-triphenylsiloxybenzyne (from o-chlorotriphenylsilyloxybenzene and lithium tetramethylpiperidide) followed by workup with aqueous acid gives the title compound m.p. 192°-3° C. (ethylacetate).

Sources & evidence

ORD record
ord-03a3805f45fa46da86d8dcc88f727809
Source dataset
uspto-grants-1981_10
Patent number
US04296029

Reaction notes

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