tert-Butyl piperazine-1-carboxylate → HCID 69417618, compound

HRID 1373552Notes

Reaction equation

C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.Br[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[F:37].[C:38]([N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].CC([O-])(C)C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:41]([O:40][C:38]([N:45]1[CH2:50][CH2:49][N:48]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][C:28]=2[F:37])[CH2:47][CH2:46]1)=[O:39])([CH3:44])([CH3:42])[CH3:43]

Participants

Conditions

Temperature: 80 °C

Procedure

A third intermediate compound, 1-(2-Fluoro-naphthalen-1-yl)-piperazine, was produced as follows: A solution of Pd(OAc)2 (44.8 mg, 0.2 mmol) and 2-(dicyclohexylphosphino)biphenyl (70.0 mg, 0.2 mmol) was degassed by bubbling N2 for 20 min. 1-Bromo-2-fluoro-naphthalene (0.448 g, 2 mmol) and 1-Boc-piperazine (0.446 g, 2.4 mmol) were added followed by the addition of NaOtBu (0.27 g, 2.8 mmol). The mixture was warmed up to 80° C. and kept at this temperature for 16 h. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel to give 4-(2-fluoro-naphthalen-1-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.24 g, 40%).

Workup

customby bubbling N2 for 20 min
customThe solvent was removed under reduced pressure
customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-8ef69b22fd054433a576220a08c1f334
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160888B2

Reaction notes

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