Naphthalene → Duloxetine

HRID 2063189Notes

Reaction equation

HRID 2063189 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C@H:5]([OH:11])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>>[CH3:1][NH:2][CH2:3][CH2:4][C@H:5]([O:11][C:20]1[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][CH:19]=1)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 931NaphthaleneHCID 100950473-(N-Methylamino)-1-(2-thienyl)-1-propanol, (-)-

Product 1

HCID 60835Duloxetine

Procedure

contacting the (S)—N-methyl-3-hydroxy-3-(2-thienyl)-1-propanamine with an activated naphthalene in a reaction mixture under conditions sufficient to produce (3S)—N-methyl-3-naphthalen-1-yloxy-3-thiophen-2-yl-propan-1 amine (Duloxetine) having the structure of formula (VIII); and (d) recovering the (3S)—N-methyl-3-naphthalen-1-yloxy-3-thiophen-2-yl-propan-1-amine from the reaction mixture.

Sources & evidence

ORD record
ord-131123ef1a814632b52455c6fcd99238
Source dataset
uspto-grants-2012_10
Patent number
US08288141B2

Reaction notes

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