Iodoethane → HCID 49854635, compound

HRID 1400053Notes

Reaction equation

HRID 1400053 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]45[CH2:24][CH:23]4[CH2:22][NH:21][CH2:20]5)=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][CH2:26]N(C(C)C)C(C)C.C(I)C>CN(C=O)C>[CH2:25]([N:21]1[CH2:22][CH:23]2[C:19]([C:16]3[CH:17]=[CH:18][C:13]([N:10]4[CH2:11][CH2:12][N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH2:8][CH2:9]4)=[CH:14][CH:15]=3)([CH2:24]2)[CH2:20]1)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 67514463HCID 67514463, compound

Product 1

HCID 49854635HCID 49854635, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trihydrochloride salt of 1-(4-(4-phenylpiperazin-1-yl)phenyl)-3-azabicyclo[3.1.0]hexane (0.92 g, 2.19 mmol) in dry DMF (6 mL) was added DIPEA (1.21 g, 6.44 mmol)) followed by addition of ethyl iodide (0.197 mL, 2.4 mmol). The reaction was stirred at r.t. for 3 h under argon. After completion of reaction as confirmed by TLC, crude compound was extracted with ethyl acetate (60 mL) and was given water washings (3×30 mL). The combined organic layers were dried over Na2SO4 and the solvents were removed in vacuo to afford the crude compound which was purified by column chromatography (silica gel 0.8:9.2 MeOH:DCM) to afford pure title compound (0.61 g, 74%).

Workup

  1. customAfter completion of reaction
  2. extractionwas extracted with ethyl acetate (60 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvents were removed in vacuo
  5. customto afford the crude compound which
  6. customwas purified by column chromatography (silica gel 0.8:9.2 MeOH:DCM)

Sources & evidence

ORD record
ord-6c445a0c4c0f402bb31f01a3856d2327
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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