Triethylamine → 2-(Benzooxazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2113508Notes

Reaction equation

HRID 2113508 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 665702372-(Benzooxazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl esterYield 110.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(RS) 2-Aminomethyl-piperidine-1-carboxylic acid tert butyl ester (0.21 g) and 2-chlorobenzoxazole (0.153 g) and triethylamine (0.1 g) were combined in tetrahydrofuran (10 ml) and stirred at room temperature for 4 hours. The mixture was partitioned between ethyl acetate and water, the organic phase dried and solvent removed at reduced pressure to give the title compound (0.36 g) as an oil that solidified on standing.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe organic phase dried
  3. customsolvent removed at reduced pressure

Sources & evidence

ORD record
ord-9242a3692f874e2aa951dcc21ba8a5ab
Source dataset
uspto-grants-2008_10
Patent number
US07432270B2

Reaction notes

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