Chloro-N,N-diethylacetamide → HCID 69418910, compound

HRID 456475Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:24][C:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[O:26]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:24][C:25](=[O:26])[N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

4-(2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (500 mg, 1.8 mmol) was dissolved in DMF (2 mL), and sodium hydride (1.98 mmol) was added. The mixture was stirred for about 10 minutes and 2-chloro-N,N-diethyl-acetamide (269 mg, 1.8 mmol) was added. The mixture was heated to 80° C. for about 2 hours. The mixture was concentrated and deprotected, which was then chromatographed to give about 395 mg of the final compound as a clear oil (75%). MS found 292.2

Workup

concentrationThe mixture was concentrated
customdeprotected, which was then chromatographed

Sources & evidence

ORD record: ord-832385cff632406ab71b3cd5f72f7742
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186715B2

Reaction notes

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