1-Acetylpiperazine → HCID 18186383, compound

HRID 1180204Notes

Reaction equation

HRID 1180204 reaction equation
Br[C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[C:86]([N:89]1[CH2:94][CH2:93][NH:92][CH2:91][CH2:90]1)(=[O:88])[CH3:87]>C1(C)C=CC=CC=1.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O.C(OCC)(=O)C>[C:86]([N:89]1[CH2:94][CH2:93][N:92]([C:2]2[CH:33]=[CH:32][C:5]([CH2:6][CH:7]3[C:16]4[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)=[CH:14][CH:15]=4)[CH2:10][CH2:9][N:8]3[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:4][CH:3]=2)[CH2:91][CH2:90]1)(=[O:88])[CH3:87]

Participants

9

Reactant 4

HCID 837951-AcetylpiperazineHCID 634876Binap, (A+-)-HCID 18186409HCID 18186409, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 18186383HCID 18186383, compoundYield 41.1%

Reagents, catalysts & solvents 4

HCID 72499888Dibenzalacetone palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(4-bromobenzyl)-6-phenylmethoxy-2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline (1.0 g, 1.99 mmol), dibenzylideneacetone palladium (36 mg, 0.04 mmol), BINAP (74 mg, 0.12 mmol), sodium tert-butoxide (0.29 g, 3.0 mmol) and N-acetylpiperazine (0.38 g, 3.0 mmol) in 2 ml of toluene were added to a sealed tube under an argon atmosphere and heated at 80° C. for 16 h. The sealed tube was cooled to room temperature and the contents of the tube transferred to a separatory funnel. Ethyl acetate and water were added and the organic layer was separated. The combined organic layers were dried over MgSO4, concentrated, and purified by column chromatography (SiO2, chloroform/methanol, 99:1) to provide the title compound (0.45 g, 41% yield): ES-MS (m/z) 550 [M+H]+.

Workup

  1. additionwere added to a sealed tube under an argon atmosphere
  2. temperatureThe sealed tube was cooled to room temperature
  3. customthe contents of the tube transferred to a separatory funnel
  4. customthe organic layer was separated
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by column chromatography (SiO2, chloroform/methanol, 99:1)

Sources & evidence

ORD record
ord-e280bae63f334660b31f139433e8dd4b
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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