Phosphine → HCID 68815759, compound

HRID 2100679Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH3:11].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].P.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.CCCCCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[CH2:10][CH3:11])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

1-Bromo-2-ethyl-4-methoxy-benzene (1 eq), piperazine-1-carboxylic acid tert-butyl ester (1.5 eq), Pd(OAc)2 (0.03 eq), phosphine ligand (0.06 eq), sodium t-butoxide (1.7 eq) are mixed in toluene and the resulting mixture is heated at 120° C. in microwave for 20 minutes. It is then diluted with EtOAc/hexane and filtered through celite. Flash column chromatography (20% EtOAc/hexane) gave 4-(2-Ethyl-4-methoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester. MS: (ES+): 321.2 (M+1)+.

Workup

filtrationfiltered through celite

Sources & evidence

ORD record: ord-d2b2efc0f48b465abab3bd08d0b67024
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572811B2

Reaction notes

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