Acetyl chloride → HCID 21963560, compound

HRID 2211895Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][CH3:25])[CH2:12][CH2:11]2)=[N:2]1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>ClC(Cl)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]([CH3:25])[C:33](=[O:35])[CH3:34])[CH2:12][CH2:11]2)=[N:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

{2-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-methyl-amine was diluted to 0.20 M with anhydrous dichloroethane, then delivered to an 8 mL vial via pipette (0.20 mmol). To the amine solution was added base (0.4 M triethylamine in dichloroethane, 0.40 mmol). Acetyl chloride was diluted to 0.20 M with dichloroethane, and added at rt (0.2 mmol). The reaction was shaken overnight at 50° C., then evaluated by MS. Polyamine scavenging resin was added (0.5 mmol). The solution was shaken overnight at rt, then filtered into an 8 mL vial. The reaction was concentrated using an HT-12 GeneVac, then purified by HPLC (30×100 mm ODS-A C(18) 5u column). N-{2-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-N-methyl-acetamide was isolated in 100% purity @ 254 nm, LCMS (APCI): 479 [M+H]+.

Workup

additionadded at rt (0.2 mmol)
stirringThe solution was shaken overnight at rt
filtrationfiltered into an 8 mL vial
concentrationThe reaction was concentrated
custompurified by HPLC (30×100 mm ODS-A C(18) 5u column)

Sources & evidence

ORD record: ord-f49fec884552421f81b652a2960dc492
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101886B2

Reaction notes

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