Acetyl chloride → HCID 13520660, compound

HRID 1249151Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]3[C:22]=2[CH2:23][CH2:24][CH2:25][NH:26]3)[CH2:15][CH2:14]1.C(N(CC)CC)C>O1CCCC1>[C:1]([N:26]1[C:27]2[C:22](=[C:21]([CH2:20][CH2:19][N:16]3[CH2:17][CH2:18][N:13]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[O:6][CH3:5])[CH2:14][CH2:15]3)[CH:30]=[CH:29][C:28]=2[OH:31])[CH2:23][CH2:24][CH2:25]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 1.45 ml of acetyl chloride is 20 ml of tetrahydrofuran is added at 5° C. to a solution of 7.34 g of 5-{2-[4-(2-methoxyphenyl)piperazinyl]ethyl}-8-hydroxy-1,2,3,4-tetrahydro quinoline in 140 ml of anhydrous tetrahydrofuran containing 2.8 ml of triethylamine. This is stirred for 2 hours at 5° C. and then for 1 hour at room temperature. Then, the insoluble substance is filtered off and concentrated to dryness under reduced pressure. The residue is purified by chromatoflash on 750 g of silica (70-230 mesh) by eluating with the mixture CH2Cl3 /CH3OH (95/5).

Workup

waitfor 1 hour at room temperature
filtrationThen, the insoluble substance is filtered off
concentrationconcentrated to dryness under reduced pressure
customThe residue is purified by chromatoflash on 750 g of silica (70-230 mesh)

Sources & evidence

ORD record: ord-afd35f3f9fdf4838899667f0a17220f9
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04629728

Reaction notes

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