Pyridine → N-[2-(2-Pyridinyl)ethyl]-4-(tetradecyloxy)benzeneacetamide

HRID 1728838Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.N1C=CC=CC=1.[CH2:16]([O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](Cl)=[O:39])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl.C(Cl)(Cl)Cl>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][NH:1][C:38](=[O:39])[CH2:37][C:34]1[CH:35]=[CH:36][C:31]([O:30][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° solution of 5.24 g of 2-(2-aminoethyl)pyridine, 13.22 ml of pyridine and 50 ml of methylene chloride is added, dropwise, 15 g of product from Example 53 in 150 ml of methylene chloride. The reaction is stirred at 0° C. for 4 hours followed by 68 hours at room temperature. The reaction is diluted with chloroform, washed with saturated sodium bicarbonate, water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:75-100% ethyl acetate/hexane) to give 8.3 g of the desired product as colorless prisms.

Workup

waitfollowed by 68 hours at room temperature
washwashed with saturated sodium bicarbonate, water and saturated sodium chloride
customdried
concentrationconcentrated in vacuo
customThe residue is purified by column chromatography (silica gel:75-100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-6076f06e61364577886c33cf714730a1
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05328921

Reaction notes

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