Triethylamine → Tert-butyl 4-(3-(4-bromophenyl)propyl)piperazine-1-carboxylate

HRID 2390551Notes

Reaction equation

HRID 2390551 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)(=O)=O.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(#N)C>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][N:19]2[CH2:18][CH2:17][N:16]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 196884663-(4-Bromophenyl)propyl methanesulphonate

Product 1

HCID 67025512Tert-butyl 4-(3-(4-bromophenyl)propyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 3-(4-bromophenyl)propyl methanesulfonate (4.2 g, 14.33 mmol) in acetonitrile (33.2 ml) was added tert-butyl piperazine-1-carboxylate (3.47 g, 18.62 mmol) and triethylamine (2.60 ml, 18.62 mmol). Reaction mixture heated to 75° C. overnight. The reaction mixture was evaporated to dryness and redissolved in EtOAc (40 mL), and washed with 2:8 saturated brine:water (45 mL). The aqueous was extracted with EtOAc (2×25 mL), organics combined and washed with 2:8 saturated brine:water (2×45 mL) and saturated brine (25 mL). 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, 50 g silica column, elution gradient 30 to 50% EtOAc in dichloromethane. Pure fractions were evaporated to dryness to afford the sub-title compound as a yellow oil. Yield: 2.4 g

Workup

  1. customReaction mixture
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionredissolved in EtOAc (40 mL)
  4. washwashed with 2:8 saturated brine
  5. extractionThe aqueous was extracted with EtOAc (2×25 mL)
  6. washwashed with 2:8 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, 50 g silica column, elution gradient 30 to 50% EtOAc in dichloromethane
  13. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-8119c57cda2c445a9ae6bb8c6e280819
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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