4-Methylmorpholine → 1-(3,5-dimethoxyphenyl)-4-(4-quinolyl-carbonyl)piperazine

HRID 1827672Notes

Reaction equation

HRID 1827672 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[CH:3][CH:2]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:48][O:49][C:50]1[CH:51]=[C:52]([N:58]2[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]2)[CH:53]=[C:54]([O:56][CH3:57])[CH:55]=1>CN(C=O)C>[CH3:48][O:49][C:50]1[CH:51]=[C:52]([N:58]2[CH2:59][CH2:60][N:61]([C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=[CH:2][CH:3]=3)=[O:13])[CH2:62][CH2:63]2)[CH:53]=[C:54]([O:56][CH3:57])[CH:55]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 102434-Quinolinecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27362051-(3,5-Dimethoxyphenyl)piperazine

Product 1

HCID 98645071-(3,5-dimethoxyphenyl)-4-(4-quinolyl-carbonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2 g (11.5 mmol) of quinoline-4-carboxylic acid were suspended in 80 ml of DMF. With stirring, 1.74 g (17.2 mmol) of N-methylmorpholine and then a solution of 8.95 g (17.2 mmol) of Py-BOP (1-benzotriazolyltripyrrolidinophosphonium hexafluorophosphate) and 2.56 g (11.5 mmol) of 1-(3,5-dimethoxyphenyl)piperazine in 25 ml of DMF were added to this mixture. The mixture was stirred at RT for 12 h, the DMF was distilled off under reduced pressure and the residue was purified on a silica gel column (Kieselgel 60, from Merck AG, Darmstadt) using the mobile phase dichloromethane/methanol/25 percent ammonia (90:10:1 v/v/v).

Workup

  1. stirringThe mixture was stirred at RT for 12 h
  2. distillationthe DMF was distilled off under reduced pressure
  3. customthe residue was purified on a silica gel column (Kieselgel 60, from Merck AG, Darmstadt)

Sources & evidence

ORD record
ord-7eed42a08ffc46bb8eab3ad475535542
Source dataset
uspto-grants-2006_06
Patent number
US07056912B2

Reaction notes

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