Dimethylformamide → HCID 86646569, compound

HRID 1698407Notes

Reaction equation

HRID 1698407 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.C([Li])CCC.CN([CH:26]=[O:27])C>>[C:14]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH:26]=[O:27])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67276276HCID 67276276, compoundHCID 178418339Butyllithium

Product 1

HCID 86646569HCID 86646569, compoundYield 105.5%

Procedure

In a manner analogous to example 1 d, the process is carried out by a reaction of 9.9 g (34 mmol) of 1-(4-bromo-2-tert-butylphenyl)piperidine with 20 ml (50 mmol) of a 2.5M solution of n-butyllithium and 3.9 ml (50 mmol) of DMF. 8.8 g of 3-tert-butyl-4-piperidin-1-ylbenzaldehyde are obtained in the form of a yellow oil (yield=100%).

Workup

  1. customanalogous to example 1 d

Sources & evidence

ORD record
ord-6cde6dd4760342f6ae3630ce458a0e1f
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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