3-Bromoquinoline → 1-Methyl-4-(quinolin-3-yl)piperidin-4-ol

HRID 4967

Reaction equation

HRID 4967 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])CCC.[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1>CCCCCC>[OH:24][C:21]1([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 214133-BromoquinolineHCID 740491-Methyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 190962031-Methyl-4-(quinolin-3-yl)piperidin-4-olYield 53.84%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

95.01 g of 3-bromoquinoline were treated with 200 ml of a 2.5M solution of butyllithium in hexane and 51.62 g of 1-methylpiperid-4-one in accordance with the procedure described in Stage A of Example 1, in order to obtain the expected product.

Sources & evidence

ORD record
ord-dbcee54bd5e04652bd5d90e8abadadc6
Source dataset
uspto-grants-1993_09
Patent number
US05242933

Linked notes

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