Benzaldehyde → 2-[3-(1-Butylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

HRID 1895960Notes

Reaction equation

HRID 1895960 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=2)[CH2:10][CH2:9]1)[C:2]1C=CC=[CH:4][CH:3]=1.C(=O)C1C=CC=CC=1>>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11](=[CH:14][C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=2)[CH2:12][CH2:13]1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 875507132-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

Product 1

HCID 875505202-[3-(1-Butylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

Procedure

The title compound was prepared following the procedure described for the compound of Example 27, but substituting butyraldehyde for benzaldehyde. After the usual work-up procedure, the crude was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with a gradient Petroleum Ether-(EtOAc+1.4 N methanolic ammonia 1:0.1) from 90:10 to 30:70 affording the title compound.

Workup

  1. customAfter the usual work-up procedure, the crude was purified by automated flash liquid chromatography (Horizon™-Biotage)
  2. washeluting with a gradient Petroleum Ether-(EtOAc+1.4 N methanolic ammonia 1:0.1) from 90:10 to 30:70 affording the title compound

Sources & evidence

ORD record
ord-2e3fe3762d6747e9bd75160e06d87cec
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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