Tributylamine → HCID 23577267, compound

HRID 1827252Notes

Reaction equation

HRID 1827252 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH2:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=1.C(N(CCCC)CCCC)CCC.COCCO>C1(O)CCCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7622TributylamineHCID 80192-MethoxyethanolHCID 27827912-Chloro-3-fluoropyridineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 23577267HCID 23577267, compound

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Procedure

A mixture of 2 mmol of 4-aminomethyl-piperidine-1-carboxylic acid benzyl ester, 1 mmol of 2-chloro-3-fluoropyridine, and 1 mmol of tributylamine were heated to reflux in 2 mL of cyclohexanol for 3 days (or 2-methoxyethanol for 14 days) under nitrogen. Preparative TLC eluting with 75:25 ether:hexane gave 4-[(3-fluoro-pyridin-2-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester:

Workup

  1. temperaturewere heated
  2. washPreparative TLC eluting with 75:25 ether

Sources & evidence

ORD record
ord-b877d2cfdaa4428986f54df19699d8a5
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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