2-Bromoethyl methyl ether → HCID 42633095, compound

HRID 417983Notes

Reaction equation

HRID 417983 reaction equation
Cl.Cl.Cl.[C:4]1([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[O:17])[CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:27][O:28][CH2:29][CH2:30]Br.CCN(C(C)C)C(C)C>CN(C=O)C>[NH3:10].[C:4]1([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH2:30][CH2:29][O:28][CH3:27])[CH2:23][CH2:22]3)=[O:17])[CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 81531DiisopropylethylamineHCID 66650707HCID 66650707, compound

Product 2

HCID 222AmmoniaHCID 42633095HCID 42633095, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

2-(piperazin-1-yl)ethyl 4-phenylpiperazine-1-carboxylate (None HCl salt of Example 30; 311 mg, 0.98 mmol) was dissolved in DMF (2 mL). 2-bromoethyl methyl ether (92 μl, 0.98 mmol) and DIPEA (0.3 mL, 1.72 mmol) were added and the reaction mixture was heated at 170° C. for 15 minutes in a Biotage Initiator microwave at high absorption. The reaction mixture was concentrated in vacuo, dissolved in 1 M aq Na2CO3 solution (25 mL) and extracted with DCM (3×25 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography (eluting with DCM, followed by a 200:8:1 mixture of DCM:EtOH:NH3) to give 2-(4-(2-methoxyethyl)-piperazin-1-yl)ethyl 4-phenylpiperazine-1-carboxylate (163 mg, 44%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in 1 M aq Na2CO3 solution (25 mL)
  3. extractionextracted with DCM (3×25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by normal phase column chromatography (
  7. washeluting with DCM
  8. additionfollowed by a 200:8:1 mixture of DCM

Sources & evidence

ORD record
ord-8e575756313a490f895e942dd0897966
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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