Triethylamine → HCID 67201414, compound

HRID 2036048Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=O)[C:22](F)(F)F)[CH2:17][CH2:16]3)=[C:11]([CH3:27])[C:9]=2[CH:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[Cl:35][C:36]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])C=1CBr.C(OCC)(=O)C.CCCCCC>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[C:36]([Cl:35])=[CH:43][CH:42]=[CH:41][C:40]=4[Cl:44])[CH2:17][CH2:16]3)=[C:11]([CH3:27])[C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 4-Methyl-5-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzofuran-2-carboxylic acid ethyl ester (0.15 g, 0.0003 mol) in dry THF was added triethyl amine (0.15 ml, 0.001 mol) and cooled to 0° C. and stirred under nitrogen. 2,6 dichloro benzyl bromide (0.107 g, 0.00045 mol) was added and stirred for 2 hours at room temperature. The completion of the reaction was confirmed by TLC. Solvent was concentrated under reduced pressure added water. The solid separated was filtered, washed with water (10 ml). After drying under vacuum, the crude product was isolated as brown solid. Column chromatography using 10/90 ethyl acetate/hexane yielded 5-[4-(2,6-Dichloro benzyl)-piperazine-1-yl]-4-methyl-benzofuran-2-carboxylic acid ethyl ester (0.13 g, 78%).

Workup

stirringstirred for 2 hours at room temperature
concentrationSolvent was concentrated under reduced pressure
additionadded water
customThe solid separated
filtrationwas filtered
washwashed with water (10 ml)
customAfter drying under vacuum
customthe crude product was isolated as brown solid

Sources & evidence

ORD record: ord-f6a377942e7649d38d00960c78c233c5
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575161B2

Reaction notes

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