Tris(1,1-dimethylethyl)phosphine → 4-(4-Benzyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2353231Notes

Reaction equation

HRID 2353231 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.O(C(C)(C)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]>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:24]2[CH:25]=[CH:26][C:21]([CH2:20][C:17]3[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=3)=[CH:22][CH:23]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27593641-Benzyl-4-iodobenzeneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 574195534-(4-Benzyl-phenyl)-piperazine-1-carboxylic acid tert-butyl esterYield 99.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1-Boc-piperazine (2.5 g, 13.1 mmol) and 4-iododiphenylmethane (4.0 g, 13.1 mmol) in toluene were added the following reagents: Pd2(dba)3 (0.36 g, 0.3 mmol), PtBu3 (0.7 g 3.0 mmol) and NaO-t-Bu (1.26 g, 13.1 mmol). The reaction mixture was stirred at ambient temperature overnight and then filtered. The filtrate was purified using silica gel chromatography (1% MeOH in CH2Cl2) to yield the title compound as a light tan oil (4.6 g, 99%): MS (ESI) m/z 353 (M+H); 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 3.08 (t, J=5.2 Hz, 4H), 3.56 (s, J=5.2 Hz, 4H), 3.91 (s, 2H), 6.85 (dd, J=2, 6.8 Hz, 2H), 7.09 (dd, J=2, 6.4 Hz, 2H), 7.16-7.19 (m, 3H), 7.25-7.29 (m, 2H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was purified

Sources & evidence

ORD record
ord-59a7e0a5e2cb41f7af3d7b41091a88ca
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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