Water → HCID 70055547, compound

HRID 1977312Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:23][CH:22]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of piperazin-1-carboxylic acid tert-butyl ester (0.64 g), 4-bromo-4′-(5-methoxypentyloxy)biphenyl (1 g), tris(dibenzylideneacetone) (chloroform) dipalladium(0) (59 mg), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.12 g) and sodium tert-butoxide (0.55 g) in toluene (10 ml) was stirred for 54 hours at 90° C. The reaction mixture was added to a mixture of water and ethyl acetate. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 4-[4′-(5-methoxypentyloxy)biphenyl-4-yl]piperazin-1-carboxylic acid tert-butyl ester (1.19 g).

Workup

dry with materialdried over magnesium sulfate
filtrationThe magnesium sulfate was filtered off
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-1372a3d535874e05aab8de4f091d370f
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232290B1

Reaction notes

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