Acetyl chloride → HCID 46179254, compound

HRID 1626054Notes

Reaction equation

HRID 1626054 reaction equation
Cl.[C:2]([O:18][CH3:19])(=[O:17])/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][C:9](=[O:16])[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:6].[C:20](Cl)(=[O:22])[CH3:21].C(N(C(C)C)CC)(C)C>ClCCl>[C:5]([O:7][CH2:8][C:9]([N:10]1[CH2:15][CH2:14][N:13]([C:20](=[O:22])[CH3:21])[CH2:12][CH2:11]1)=[O:16])(=[O:6])/[CH:4]=[CH:3]/[C:2]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86639351HCID 86639351, compound

Product 1

HCID 46179254HCID 46179254, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-oxo-2-piperazinylethyl (2E)but-2-ene-1,4-dioate hydrochloride (14) (0.20 g, 0.68 mmol) was reacted with acetyl chloride (AcCl) (0.60 mL, 0.66 g, 0.84 mmol) and diisopropylethylamine (0.70 mL, 0.52 g, 4.0 mmol) in dichloromethane (DCM). Following aqueous work-up, the crude product was purified by silica gel flash chromatography to afford 0.12 g (54% yield) of the title compound (16) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 6.98-6.93 (m, 2H), 4.86 (s, 2H), 3.83 (s, 3H), 3.66 3.63 (m, 4H), 3.50-3.40 (m, 4H), 2.14 (s, 3H). MS (ESI): m/z 299.12 (M+H)+.

Workup

  1. customFollowing aqueous work-up, the crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-811b60823f4949b1b6f8c68a9d03e5d5
Source dataset
uspto-grants-2014_07
Patent number
US08785443B2

Reaction notes

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