4-Toluenesulfonyl chloride → HCID 21255123, compound

HRID 636560Notes

Reaction equation

HRID 636560 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15](O)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:18]1([CH3:28])C=CC(S(Cl)(=O)=O)=CC=1.Cl/C(=C\C)/[C:31]#[N:32]>C(N(CC)CC)C>[CH3:18][C:28]1[C:15]([C:31]#[N:32])=[C:10]2[N:9]([C:1]=1[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:14][CH2:13][CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 162282641-(Pyridine-3-carbonyl)piperidine-2-carboxylic acidHCID 86756453HCID 86756453, compound

Product 1

HCID 21255123HCID 21255123, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Methyl-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile is prepared as described in Example 1, from 11.7 g of N-nicotinoyl piperidine-2-carboxylic acid (prepared according to European Patent Application EP 118321), 10 g of paratoluenesulphonyl chloride, from 24.6 cm3 of triethylamine and from 4.8 cm3 of 2-chlorocrotononitrile. 4.3 g of 2-methyl-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile are thus obtained in the form of a white powder melting at 125° C. 1.7 g of a 70/30 mixture of this compound and of its regioisomer, 1-methyl-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile are also obtained.

Workup

  1. custom2-Methyl-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carbonitrile is prepared

Sources & evidence

ORD record
ord-495d43b7fce24a7995baf5d9ef2eaf0b
Source dataset
uspto-grants-2001_02
Patent number
US06194426B1

Reaction notes

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