Trifluoroacetic acid → HCID 18919889, compound

HRID 1291077Notes

Reaction equation

HRID 1291077 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].FC(F)(F)C(O)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:30]([N:37]1[CH2:42][CH2:41][CH:40](O)[CH2:39][CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH:40]1[CH2:39][CH2:38][N:37]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:42][CH2:41]1)=[O:5]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 729302-Aminonicotinic acidHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919889HCID 18919889, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.14 g (0.00101 mol) of 2-amino-nicotinic acid was suspended in 50 ml of THF and treated with 0.077 ml (0.00101 mol) of trifluoroacetic acid. The mixture was stirred at room temperature for 1 hr., whereby a solution resulted. To this was added 0.25 g (0.0015 mol) of carbonyidiimidazole and the mixture was stirred at room temperature for 2 hrs. Subsequently, 0.34 g (0.00178 mol) of 1-benyl-4-hydroxy-piperidine was added and the mixture was stirred at 60° for 72 hrs. After removing the solvent the residue was chromato-graphed over silica gel with ethyl acetate/hexane (1:1) as the eluent. 0.105 g (31%) of 1-benzyl-piperidin-4-yl 2-amino-nicotinate was obtained as white crystals. MS: me/e (% basic peak)=311 (C18H21N3O2+, 7.5), 173 (42), 91 (100), 82 (86).

Workup

  1. custom, whereby a solution resulted
  2. stirringthe mixture was stirred at room temperature for 2 hrs
  3. stirringthe mixture was stirred at 60° for 72 hrs
  4. customAfter removing the solvent the residue

Sources & evidence

ORD record
ord-33578e63dc914d1ca2d709c8ab08f154
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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