Acetyl chloride → HCID 86753052, compound

HRID 2392576Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19]N)[CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:21]=1.C([N:24](CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:30][C:29]([NH2:24])=[O:31])[CH2:12][CH2:11]3)=[CH:8][S:7][C:6]=2[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 4-(6-fluorobenzo[b]thien-3-yl)-1-piperazine-butanamine (3.13 g, 10.2 mmol), triethylamine (1.45 g, 14.3 mmol), and dichloromethane (60 mL) under a nitrogen atmosphere was added acetyl chloride (0.883 g, 11.3 mmol) rapidly. The reaction was stirred at 0° C. for 2 hours and then at room temperature for an additional 1 hour. The reaction was diluted with dichloromethane (140 mL), washed with 5% aqueous NaOH (100 mL), and dried (K2CO3). The solvent was removed in vacuo to give a brown solid. The crude product was chromatographed on silica gel with 10% methanol/dichloromethane as eluent to afford a tan solid. Recrystallization from ethyl acetate gave 1.85 g (52%) of the title compound as beige crystals: m.p.=141 °-142° C.

Workup

waitat room temperature for an additional 1 hour
washwashed with 5% aqueous NaOH (100 mL)
dry with materialdried (K2CO3)
customThe solvent was removed in vacuo
customto give a brown solid
customThe crude product was chromatographed on silica gel with 10% methanol/dichloromethane as eluent
customto afford a tan solid
customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-d18d5791a2504ca59ccd1daef5588242
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05801176

Reaction notes

Loading…