Diethyl Ether → HCID 18918631, compound

HRID 1290518Notes

Reaction equation

HRID 1290518 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]([O:9][CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.C(OCC)C>C(#N)C>[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:30][CH2:31][N:32]([CH2:2][C:3]([C:5]3[CH:22]=[CH:21][C:8]([O:9][CH2:10][C:11]([NH:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:33][CH2:34]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 705171-(4-Pyridyl)piperazineHCID 18918598HCID 18918598, compound

Product 1

HCID 18918631HCID 18918631, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-[4-(bromoacetyl)phenoxy]-N-(phenylmethyl)acetamide (1.40 g) (preparation described in EPO 052442) in acetonitrile (5 ml) was added to a stirred solution of 1-(4-pyridyl)piperazine (1.14 g) in acetonitrile (20 ml). After stirring overnight the liquors were decanted from the residual gum, then concentrated in vacuo. Purification by flash chromatography on silica, eluting with 2 to 5% v/v methanol/dichloromethane, gave a solid. Trituration of this solid with diethyl ether gave the title compound, 95 mg: m.p. 150°-151° C.; NMR (d6DMSO) δ8.67(1H,bt) 8.15(2H,d), 8.00(2H,d), 7.26(5H,m), 7.06(2H,d), 6.81(2H,d), 4.66(2H,s), 4.34(2H,d), 3.84(2H,s), 3.33(4H,t), 2.54(4H,t); m/e 445 (M+H)+ ; calculated for C26H28N4O3. 0.25H2O: C, 69.5; H, 6.4; 12.5. found: C, 69.6; H, 6.4; N, 12.3%.

Workup

  1. customwere decanted from the residual gum
  2. concentrationconcentrated in vacuo
  3. customPurification by flash chromatography on silica
  4. washeluting with 2 to 5% v/v methanol/dichloromethane
  5. customgave a solid

Sources & evidence

ORD record
ord-d6dd68b95cde401a9d54735a6515ef6e
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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