1-(Bicyclo[2.2.1]hept-5-en-2-yl)-3-(piperidin-1-yl)propan-1-one → Biperiden

HRID 1796694Notes

Reaction equation

HRID 1796694 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8](=[O:17])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[C:18]1([Mg])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH:18]1[CH:19]=[CH:20][C:21]([C:8]([OH:17])([CH:2]2[CH:1]3[CH:6]=[CH:5][CH:4]([CH2:7]3)[CH2:3]2)[CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 121479881-(Bicyclo[2.2.1]hept-5-en-2-yl)-3-(piperidin-1-yl)propan-1-oneHCID 178507003HCID 178507003, compound

Product 1

HCID 2381Biperiden

Procedure

It has been possible to achieve this object by a method for producing biperiden by reacting 1-(bicyclo[2.2.1]hept-5-en-2-yl)-3-piperidino-1-propanone (II) with an exo/endo ratio of at least 2.5:1 with a phenylmagnesium compound to give a biperiden (Ia)-containing mixture of isomers of 1-(bicyclo-[2.2.1]hept-5-en-2-yl)-1-phenyl-3-piperidino-1-propanol (I), characterized in that the isolation of biperiden (Ia) from the mixture of isomers comprises the following steps:

Sources & evidence

ORD record
ord-be1eb52dd81e4225a8b52dd1400a8ff7
Source dataset
uspto-grants-2006_04
Patent number
US07030247B2

Reaction notes

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