Benzoyl chloride → n-(1-Benzoylpiperidin-4-yl)-n'-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}urea

HRID 1371453Notes

Reaction equation

HRID 1371453 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:11][C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH:18]([CH2:22][NH:23][C:24]([NH:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:25])[CH2:17]1.C(N(CC)C(C)C)(C)C>ClCCl>[C:1]([N:30]1[CH2:31][CH2:32][CH:27]([NH:26][C:24]([NH:23][CH2:22][CH:18]2[O:19][CH2:20][CH2:21][N:16]([CH2:15][C:14]3[CH:33]=[CH:34][C:35]([Cl:36])=[C:12]([Cl:11])[CH:13]=3)[CH2:17]2)=[O:25])[CH2:28][CH2:29]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 17984664HCID 17984664, compound

Product 1

HCID 17984690n-(1-Benzoylpiperidin-4-yl)-n'-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Benzoyl choride (0.014 ml) was added to a solution of Intermediate 16 (0.04 g) and N,N-diisopropylethylamine (0.048 ml) in dichloromethane (3 ml). The solution was stirred for 5 h at 23° C. The solvent was removed in vacuo and the residue purified by solid phase extraction (Isolute SCX sulphonic acid column) eluting with methanol followed by 10% 0.880 ammonia solution in methanol. The basic fraction was concentrated in vacuo and the residue was further purified using a silica gel solid phase extraction cartridge (1 g Varian Bond Elut), eluting sequentially with dichloromethane, ethyl acetate, acetone, acetonitrile, and methanol, to give the title compound as a clear gum (0.024 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by solid phase extraction (Isolute SCX sulphonic acid column)
  3. washeluting with methanol
  4. concentrationThe basic fraction was concentrated in vacuo
  5. customthe residue was further purified
  6. extractiona silica gel solid phase extraction cartridge (1 g Varian Bond Elut)
  7. washeluting sequentially with dichloromethane, ethyl acetate, acetone, acetonitrile, and methanol

Sources & evidence

ORD record
ord-ea26f59dc24c48f59bbc5afc970af945
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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