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

HRID 18073

Reaction equation

HRID 18073 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-97882efc0c7c4fa1915436993b0beb93
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Linked notes

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