Toluene → 4-[4-(3-Piperidin-1-yl-propoxy)-phenyl] piperazine-1-carboxylic acid cyclopropylamide

HRID 1434583Notes

Reaction equation

HRID 1434583 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23](Cl)(Cl)=[O:24].C1(C)C=CC=CC=1.C(N(CC)CC)C.[CH:41]1([NH2:44])[CH2:43][CH2:42]1>ClCCl>[CH:41]1([NH:44][C:23]([N:20]2[CH2:19][CH2:18][N:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:12][CH:13]=3)[CH2:22][CH2:21]2)=[O:24])[CH2:43][CH2:42]1

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 99240131-[4-(3-Piperidin-1-ylpropoxy)phenyl]piperazine

Product 1

HCID 579357814-[4-(3-Piperidin-1-yl-propoxy)-phenyl] piperazine-1-carboxylic acid cyclopropylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(3-piperidin-1-yl-propoxy)-phenyl]-piperazine (D11) (150 mg, 0.49 mM) in dry dichloromethane (3 ml) was added drop wise a 20% solution of phosgene in toluene (0.5 ml; −2 eq) and the resulting mixture stirred for 1 hour. The solvent was removed by evaporation and the resulting white powder dissolved in dry dichloromethane (4 ml). Triethylamine (0.14 ml: 2 eq) was added followed by cyclopropylamine (0.1 ml; 3 eq) and the mixture stirred for 18 hours. The solvent was removed by evaporation in vacuo and the residue purified on a silica column eluting with 3% methanol in dichloromethane to afford the title compound as a white solid (155 mg) MS (ES+) m/e 387 [M+H]+.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe resulting white powder dissolved in dry dichloromethane (4 ml)
  3. stirringthe mixture stirred for 18 hours
  4. customThe solvent was removed by evaporation in vacuo
  5. customthe residue purified on a silica column
  6. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-54ddf54235e942fd9103ddc6e38f9bd9
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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