Triethylamine → Tert-butyl 4-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)piperazine-1-carboxylate

HRID 2390552Notes

Reaction equation

HRID 2390552 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:31][C:32]1([CH3:39])[C:36]([CH3:38])([CH3:37])[O:35][BH:34][O:33]1>C(#N)C>[CH3:31][C:32]1([CH3:39])[C:36]([CH3:38])([CH3:37])[O:35][B:34]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:4][CH:3]=2)[O:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 67025512Tert-butyl 4-(3-(4-bromophenyl)propyl)piperazine-1-carboxylate

Product 1

HCID 67026379Tert-butyl 4-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tert-butyl 4-(3-(4-bromophenyl)propyl)piperazine-1-carboxylate (2.4 g, 6.26 mmol) in acetonitrile (12 ml) was added triethylamine (2.62 ml, 18.78 mmol) and Pd-118 (0.122 g, 0.19 mmol). Reaction mixture was stirred at RT under nitrogen for 10 min. 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (1.363 ml, 9.39 mmol) added and reaction mixture heated to 80° C. for 1 h. The reaction mixture was evaporated to dryness and redissolved in EtOAc and washed with water and saturated brine. The organic was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography using Isco Companion, 100 g silica column, elution gradient 40 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford sub-title compound as a brown oil. Yield: 0.9 g

Workup

  1. customReaction mixture
  2. customreaction mixture
  3. temperatureheated to 80° C. for 1 h
  4. customThe reaction mixture was evaporated to dryness
  5. dissolutionredissolved in EtOAc
  6. washwashed with water and saturated brine
  7. dry with materialThe organic was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto afford crude product
  11. customThe crude product was purified by flash silica chromatography
  12. washIsco Companion, 100 g silica column, elution gradient 40 to 100% EtOAc in isohexane
  13. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-1a34645d83d54969bd648f89a6326254
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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