Pyridine → N-{[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}pentanamide

HRID 2212026Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH2:13])[CH2:7]1.N1C=CC=CC=1.[C:24](Cl)(=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of Intermediate 9 (0.028 g) in dichloromethane (2 ml) containing a suspension of polyvinyl pyridine (0.1 g) was treated with valeryl chloride (0.018 ml), and the mixture was shaken at 20° C. for 16 h. Tris (2-aminoethyl)amine polystyrene scavenger resin (Argonaut Technologies, 4.46 mmol/g; 0.067 g) was added, and the mixture was shaken at 20° C. for 2 h. The mixture was filtered and the filtrate applied directly to a silica gel cartridge (1 g Varian Bond Elut). Elution with chloroform, ether, and ethyl acetate gave the title compound (0.0225 g).

Workup

stirringthe mixture was shaken at 20° C. for 2 h
filtrationThe mixture was filtered
washElution with chloroform, ether, and ethyl acetate

Sources & evidence

ORD record: ord-884f12e42e3a4aef81dc092e55a8b69e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101882B2

Reaction notes

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