Ethyl bromoacetate → Ethyl (1,4-diazepan-1-yl)acetate

HRID 2245863Notes

Reaction equation

HRID 2245863 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CC#N>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 13057080Ethyl (1,4-diazepan-1-yl)acetateYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium carbonate (1.27 g) was added to a solution of homopiperazine (5.99 g; 5 eq.) and ethyl bromoacetate (2.0 g; 1 eq.) in CH3CN (120 mL). The reaction was stirred at room temperature for 6 h. The reaction mixture was filtered thru a celite pad. The filtrate was concentrated. The remaining residual was dissolved in CHCl3 (120 mL), washed by H2O (50 mL×3) and brine (50 mL×1), dried by Na2SO4 and concentrated to give [1,4]diazepan-1-yl-acetic acid ethyl ester (1.794 g), which was carried on for the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 4.15 (m, 2H), 3.39 (s, 2H), 2.91 (m, 4H), 2.81 (m, 4H), 1.76 (m, 3H), 1.25 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. dissolutionThe remaining residual was dissolved in CHCl3 (120 mL)
  4. washwashed by H2O (50 mL×3) and brine (50 mL×1)
  5. dry with materialdried by Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-78b02ea4d1f447b4847b962af5dc8b01
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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