Acetyl chloride → HCID 46179254, compound

HRID 1685617Notes

Reaction equation

HRID 1685617 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-2cf07b63fd364dab98af1722c29314b8
Source dataset
uspto-grants-2012_04
Patent number
US08148414B2

Reaction notes

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