Triethylamine → (+)-4-{4-[3-(3-Benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile

HRID 2354561Notes

Reaction equation

HRID 2354561 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:19])[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]3)=[CH:28][C:23]=2[O:22][CH2:21]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][N:32]([CH2:3][CH2:2][C:1]([N:5]4[CH2:6][CH2:7][N:8]([C:11]5[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:19])[CH:12]=5)[CH2:9][CH2:10]4)=[O:4])[CH2:31]3)=[CH:28][C:23]=2[O:22][CH2:21]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 170395273-Benzo[1,3]dioxol-5-ylmethyl-piperidineHCID 684518974-(4-Acryloylpiperazin-1-yl)-2-fluorobenzonitrile

Product 1

HCID 12000651(+)-4-{4-[3-(3-Benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-acryloyl-piperazin-1-yl)-2-fluoro-benzonitrile (0.125 g, 0.48 mmol), (+)-3-benzo[1,3]dioxol-5-ylmethyl-piperidine (0.106 g, 0.48 mmol) and triethylamine (0.088 ml, 0.629 ml) in THF (1.6 ml) is stirred at rt for 25 h. The mixture is diluted with CH2Cl2 and washed with sat. aq. Na2CO3 solution The organic layer is separated off, dried over Na2SO4 and evaporated. The residue is purified by MPLC (60 g silica gel, eluent CH2Cl2:MeOH 9:1) to give the title compound, (+)-4-{4-[3-(3-benzo[1,3]dioxol-5-ylmethyl-piperidin-1-yl)-propionyl]-piperazin-1-yl}-2-fluoro-benzonitrile, as a colourless foam:

Workup

  1. washwashed with sat. aq. Na2CO3 solution The organic layer
  2. customis separated off
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue is purified by MPLC (60 g silica gel, eluent CH2Cl2:MeOH 9:1)

Sources & evidence

ORD record
ord-70f296480ab64e799f1e9dcefb154d27
Source dataset
uspto-grants-2010_07
Patent number
US07754719B2

Reaction notes

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