Water → HCID 21221013, compound

HRID 1584892Notes

Reaction equation

HRID 1584892 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[NH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].O>ClCCl>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([CH2:12][NH:11][C:8]([C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)=[O:9])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 21221013HCID 21221013, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-pyridinecarbonyl chloride hydrochloride (3.87 g) in dichloromethane (100 ml) was added to a suspension of 4-(aminomethyl)-1-tert-butoxycarbonylpiperidine (5.0 g) and potassium carbonate (10 g) in dichloromethane (100 ml), and the mixture stirred at ambient temperature for 2 hours before pouring into water (500 ml). The organic layer was washed with water (250 ml), dried over magnesium sulphate and the solvent was evaporated. The residue was purified by flash chromatography over silica eluting with a 20:1 mixture of dichloromethane and methanol. Appropriate fractions were combined and the solvent removed in vacuo to give N-[(1-tert-butoxycarbonyl-4-piperidyl)methyl]pyridine-3-carboxamide (3.22 g) as an orange oil.

Workup

  1. washThe organic layer was washed with water (250 ml)
  2. dry with materialdried over magnesium sulphate
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash chromatography over silica eluting with a 20:1 mixture of dichloromethane and methanol
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c0e16ec70d5f4b2d804cf99f58252d4e
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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