Triethylamine → 1-(5-Cyanopyrid-2-yl)-4-[4-(methoxycarbonylmethyl)-piperidinocarbonyl]-piperidine

HRID 1756997Notes

Reaction equation

HRID 1756997 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][N:11]=2)[CH2:6][CH2:5]1)([OH:3])=O.Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([N:7]2[CH2:8][CH2:9][CH:4]([C:1]([N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]3)=[O:3])[CH2:5][CH2:6]2)=[N:11][CH:12]=1)#[N:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 162274741-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acidHCID 18423605Methyl (piperidin-4-yl)acetate--hydrogen chloride (1/1)

Product 1

HCID 193915041-(5-Cyanopyrid-2-yl)-4-[4-(methoxycarbonylmethyl)-piperidinocarbonyl]-piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.3 g of 4-carboxy-1-(5-cyanopyrid-2-yl)-piperidine, 2.0 g of methyl 4-piperidylacetate hydrochloride, 4.8 g of 2-[(1H)-benzotriazol-1-yl]-1,1,3,3-tetramethyl-uronium tetrafluoroborate and 5 ml of triethylamine in 75 ml of dimethylformamide is stirred at ambient temperature for 16 hours. The solvent is removed under reduced pressure. The residue is diluted with water and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water and saturated saline solution and dried over sodium sulphate. The solvent is removed under reduced pressure and the residue is chromatographed over silica gel. Yield: 2.75 g (74% of theory), Melting point: 112°-115° C. Rf value: 0.40 (silica gel; methylene chloride/methanol=15:1)

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionThe residue is diluted with water
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe organic phase is washed with water and saturated saline solution
  5. dry with materialdried over sodium sulphate
  6. customThe solvent is removed under reduced pressure
  7. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-3b37f02aa62b44c9bc96f65f48ed277a
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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