4-Methylmorpholine → HCID 44197838, compound

HRID 2065536Notes

Reaction equation

HRID 2065536 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.Cl.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[CH2:43][N:42]3[CH:44]=[C:45]([C:47]([OH:49])=O)[N:46]=[C:41]3[CH2:40][CH2:39]2)=[CH:34][C:33]=1[CH3:50].[CH2:51]([CH:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CN(C=O)C>[CH2:51]([CH:58]1[CH2:63][CH2:62][N:61]([C:47]([C:45]2[N:46]=[C:41]3[CH2:40][CH2:39][CH:38]([C:35]4[CH:36]=[CH:37][C:32]([F:31])=[C:33]([CH3:50])[CH:34]=4)[CH2:43][N:42]3[CH:44]=2)=[O:49])[CH2:60][CH2:59]1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 317384-BenzylpiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68908404HCID 68908404, compound

Product 1

HCID 44197838HCID 44197838, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBTU (295 mg; 0.92 mmol) and N-methylmorpholine (253 μl; 232 mg; 2.3 mmol) were added to a solution of 6-(4-fluoro-3-methylphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-2-carboxylic acid hydrochloride (210 mg; 0.68 mmol) in DMF (1 ml). The reaction mixture was stirred vigorously for 30 min at room temperature and then 4-benzylpiperidine (162 μl; 161 mg; 0.9 mmol) was added. The reaction mixture was stirred for 4 h at room temperature and then poured onto water. The precipitated solid was filtered out and washed with petroleum ether. Yield: 205 mg (72%)

Workup

  1. stirringThe reaction mixture was stirred for 4 h at room temperature
  2. additionpoured onto water
  3. filtrationThe precipitated solid was filtered out
  4. washwashed with petroleum ether

Sources & evidence

ORD record
ord-46a16a28c1c64135b880e9cf075fbeb4
Source dataset
uspto-grants-2012_10
Patent number
US08288424B2

Reaction notes

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