1-(4-Iodophenethyl)pyrrolidine → 3-[4-(2-Pyrrolidin-1-ylethyl)phenyl]propynoic acid-(4-prop-1-ynylphenyl)amide

HRID 735033Notes

Reaction equation

HRID 735033 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[C:12]#[CH:13])=[CH:6][CH:5]=1)#[C:2][CH3:3].I[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=1>ClCCl.CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[C:12]#[C:13][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:20][CH:21]=2)=[CH:6][CH:5]=1)#[C:2][CH3:3]

Participants

4

Reactant 2

HCID 688158361-(4-Iodophenethyl)pyrrolidineHCID 86060737Propynoic acid-(4-prop-1-ynylphenyl)amide

Product 1

HCID 578457533-[4-(2-Pyrrolidin-1-ylethyl)phenyl]propynoic acid-(4-prop-1-ynylphenyl)amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.1.e. from propynoic acid-(4-prop-1-ynylphenyl)amide and 1-[2-(4-iodophenyl)ethyl]pyrrolidine. Yield: 20 mg (11% of theory); melting point: 198° C.-199° C.; C24H24N2O (M=356.47); Rf value: 0.1 (silica gel, dichloromethane/methanol (10:1))

Workup

  1. customPrepared analogously to Example 2.1.e

Sources & evidence

ORD record
ord-aadc41fb2d6c44f58defe4738fd0823d
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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