Dichloromethane → HCID 12433017, compound

HRID 840410Notes

Reaction equation

HRID 840410 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[CH:5][CH:4]=1)#[N:2].C(Cl)[Cl:17].C(Cl)(=O)C(Cl)=O>CN(C=O)C>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([Cl:17])=[O:15])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 124330104-Cyanonaphthalene-1-carboxylic acid

Product 1

HCID 12433017HCID 12433017, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 4-cyano-1-naphthoic acid (0.090 g, 0.45 mmol), DCM (3 mL), oxalyl chloride (0.063 g, 0.50 mmol) and DMF (approximately 5 μL) was stirred for 3 h and concentrated to provide 4-cyano-1-naphthoyl chloride as an off-white solid which was used directly. Using standard acylation conditions 4-cyano-1-naphthoyl chloride (0.090 g) was reacted with N-[(S)-2-(3,4-dichlorophenyl)-4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-methylamine to afford the free base (0.215 g) which was converted to the citrate salt.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-5c0fc18c890447aa8dde66f105280299
Source dataset
uspto-grants-2002_04
Patent number
US06365602B1

Reaction notes

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