tert-Butyl methyl ether → HCID 86690645, compound

HRID 1505612Notes

Reaction equation

HRID 1505612 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:4][CH:3]=1.COC(C)(C)C.CC(C)([O-])C.[Na+].[N:32]1([C:38](=[O:40])[CH3:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1.O1CCOCC1>[C:38]([N:32]1[CH2:37][CH2:36][N:35]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:12])=[O:11])=[CH:4][CH:3]=2)[CH2:34][CH2:33]1)(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 837951-AcetylpiperazineHCID 23676156Sodium t-butoxideHCID 61401001HCID 61401001, compound

Product 1

HCID 86690645HCID 86690645, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylCatalystHCID 312751,4-DioxaneSolvent

Procedure

In a flask, N-[(4-bromophenyl)methyl]-1-phenyl-methanesulfonamide (2.79 g, 8.20 mmol), chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)[2-(2 aminoethylphenyl)]palladium(II), methyl-t-butylether adduct (60 mg, 0.082 mmol), 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl (39 mg, 0.0820 mmol) and sodium tert-butoxide (1.22 g, 12.3 mmol) were combined and purged with nitrogen. 1,4-Dioxane (40 mL) and 1-piperazin-1-ylethanone (1.58 g, 12.3 mmol) were then added and the reaction was stirred at ambient temperature for 16 hours. The precipitate was collected by filtration, washed with DCM and then with water and dried under vacuum overnight to give N-[[4-(4-acetylpiperazin-1-yl)phenyl]methyl]-1-phenyl-methanesulfonamide (1.52 g, 48% yield). LCMS (m/z) ES+ 388.2 [M+1]+.

Workup

  1. custompurged with nitrogen
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with DCM
  4. dry with materialwith water and dried under vacuum overnight

Sources & evidence

ORD record
ord-8f06ce542d414567b635d26f6b529377
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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