Acetyl chloride → HCID 21963235, compound

HRID 2211896Notes

Reaction equation

HRID 2211896 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][CH:25]([CH3:27])[CH3:26])[CH2:12][CH2:11]2)=[N:2]1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>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]([CH:25]([CH3:27])[CH3:26])[C:35](=[O:37])[CH3:36])[CH2:12][CH2:11]2)=[N:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 21963415HCID 21963415, compound

Product 1

HCID 21963235HCID 21963235, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

{2-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-isopropyl-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 three days, with the temperature ramped from 50° C. to 85° C. An additional 0.20 mmol of acetyl chloride was added after the second day. Polyamine scavenging resin was added (0.5 mmol). The solution was shaken overnight at room temperature, and filtered into an 8 mL vial. The reaction was concentrated via 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-isopropyl-acetamide was isolated in 100% purity @ 254 nm, LCMS (APCI): 423 [M+H]+.

Workup

  1. additionadded at rt (0.2 mmol)
  2. customramped from 50° C. to 85° C
  3. stirringThe solution was shaken overnight at room temperature
  4. filtrationfiltered into an 8 mL vial
  5. concentrationThe reaction was concentrated via HT-12 GeneVac
  6. custompurified by HPLC (30×100 mm ODS-A C(18) 5u column)

Sources & evidence

ORD record
ord-1aa4f1c5a85c4d0686f355f87699efff
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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