tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine-1-carboxylate

HRID 1723824Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:11][C:10]([F:13])([F:12])[CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-bromo-4-(2,2,2-trifluoroethoxy)benzene (14.5 g, 57 mmol) was dissolved in toluene (250 ml) under an argon atmosphere. tert-Butyl piperazine-1-carboxylate (12.7 g, 68 mmol), sodium tert-butoxide (7.6 g, 79.5 mmol) rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (200 mg, 0.32 mmol) and tris(dibenzylideneacetone)dipalladium(0) (200 mg, 0.2 mmol) were added and the reaction heated to 80° C. for 4 hours. The mixture was then cooled and filtered through Celite to yield crude tert-butyl 4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine-1-carboxylate (32.47 g).

Workup

temperatureThe mixture was then cooled
filtrationfiltered through Celite

Sources & evidence

ORD record: ord-bac93926368140a48b59c251a168a7f3
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485644B2

Reaction notes

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