Potassium Carbonate → 1-Tert-butoxycarbonyl-4-(2-fluoroethyl)homopiperazine

HRID 1062562Notes

Reaction equation

HRID 1062562 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][CH2:17][F:18].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:16][CH2:17][F:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 222814761-Tert-butoxycarbonyl-4-(2-fluoroethyl)homopiperazineYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-tert-butoxycarbonylhomopiperazine (800 mg, 3.99 mmol), 1-bromo-2-fluoroethane (0.46 mL, 11.98 mmol) and potassium carbonate (1.10 g, 7.98 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred overnight at 70° C. and was cooled to room temperature. The reaction mixture was filtered through a Celite pad, and the filtrate was evaporated to dryness under vacuum to afford yellowish oil. The crude product was purified by MPLC on silica gel (3% MeOH in CHCl3) to afford the titled compound (653 mg, 67%) as a pale yellow oil.

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. customthe filtrate was evaporated to dryness under vacuum
  4. customto afford yellowish oil
  5. customThe crude product was purified by MPLC on silica gel (3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-9ce85a3592c74161b68e9c353c0cbd22
Source dataset
uspto-grants-2005_11
Patent number
US06962911B2

Reaction notes

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