Sodium Azide → 3-Azidomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene

HRID 556145Notes

Reaction equation

HRID 556145 reaction equation
Br[CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:4]1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:4]1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 248577553-Bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene2×

Product 1

HCID 248577563-Azidomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Referring to Scheme 2, acylation of the alpha-tetralone 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (Compound 1) with diethylcarbonate was followed by reduction with triethylsilane to give 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl ester (Compound 10). Reduction and conversion to 3-bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene (Compound 12) is followed by alkylation with sodium azide in DMF to give 3-azidomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene (Compound 13). Chiral separation of Compound 13 is followed by hydrogenation to give a compound of the invention, C-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methylamine (Compound 14). Alternatively, reduction and conversion to 3-bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene (Compound 12) is followed by alkylation with substituted amines to give 1-phenyl-3-aminoalkyl-1,2,3,4-tetrahydronaphthalenes (Compound 15).

Sources & evidence

ORD record
ord-4b1205da1e6c46ddad9628094d17c754
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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