Benzylamine → HCID 69736395, compound

HRID 896549Notes

Reaction equation

HRID 896549 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH2:6][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:9][C:10]=1[NH:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:4]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 69736395HCID 69736395, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 4-oxopiperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (2.57 g, 10 mmol), benzylamine (1.20 mL, 11 mmol) and p-toluenesulfonic acid hydrate (19 mg, 0.1 mmol) in toluene (40 mL) was heated at reflux under a Dean-Stark trap for 22.75 hours. The mixture was cooled to room temperature and concentrated under vacuum to provide a yellow gummy solid (3.86 g), used without further purification. 1H NMR (300 MHz, CDCl3) δ9.25 (bt, J=6 Hz, 1H), 7.4-7.1 (m, 5H), 4.42 (d, J=6 Hz, 2H), 4.11 (s, 2H), 3.71 (s, 3H), 3.49 (t, 2H), 2.38 (m, 2H), 1.48 (s, 9H).

Workup

  1. temperatureat reflux under a Dean-Stark trap for 22.75 hours
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-43cbdefec3fb4b7bb4b00d1762941126
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

Loading…