Sodium Carbonate → HCID 68697673, compound

HRID 2245865Notes

Reaction equation

HRID 2245865 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][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC#N>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][N:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:23]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 68163Hexahydro-1,4-diazepineHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 68697673HCID 68697673, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium carbonate (2.12 g) was added to the solution of homopiperazine (10.0 g; 5 eq.) and ethyl 5-bromovalerate (4.18 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 5-[1,4]diazepan-1-yl-pentanoic acid ethyl ester (4.0 g), which was carried on for the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 4.09 (q, 2H, J=7.0 Hz), 2.90 (m, 4H), 2.63 (m, 4H), 2.47 (t, 2H, J=7.0 Hz), 2.29 (t, 2H, J=7.0 Hz), 2.07 (bs, 1H), 1.73 (m, 2H), 1.60 (m, 2H), 1.48 (m, 2H), 1.22 (t, 3H, J=7.0 Hz).

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-09b05a0ac927438f94f886a04d9a2eaf
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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