Benzyl Bromide → [(1-Nitrocyclohexyl)methyl]benzene

HRID 849312

Reaction equation

[N+:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([O-:3])=[O:2].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+]>>[CH2:10]([C:4]1([N+:1]([O-:3])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 7498Benzyl Bromide

HCID 14285Nitrocyclohexane

HCID 24758Sodium hydride

Product 1

HCID 4560895[(1-Nitrocyclohexyl)methyl]benzene

Procedure

Nitrocyclohexane and benzylbromide are subjected to condensation reaction in the presence of sodium hydride to obtain 1-benzyl-1-nitrocyclohexane. The product is reduced with lithium aluminum hydride to obtain 1-benzyl-1-aminocyclohexane. The product is reacted with methyl chloroformate to obtain 1-benzyl-1-methoxycarbonylaminocyclohexane, and the product is subjected to intramolecular cyclization in the presence of phosphorous oxychloride to obtain spiro[1,2,3,4-tetrahydroisoquinoline-2,1'-cyclohexan]-1-one.

Sources & evidence

ORD record: ord-a509166e4efc4db083be2698328e757b
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011150

Linked notes

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