Triethylamine → HCID 69737932, compound

HRID 896517Notes

Reaction equation

HRID 896517 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH2:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1([O:22][C:23](=O)[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]3[N:35]([CH3:36])[N:34]=[N:33][N:32]=3)[CH:26]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:23]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]3[N:35]([CH3:36])[N:34]=[N:33][N:32]=3)[CH:26]=2)=[O:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamate

Product 1

HCID 69737932HCID 69737932, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-aminomethylpiperidine-1-carboxylic acid tert-butyl ester (1.81 g, 8.47 mmol), [3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester (2.50 g, 8.47 mmol), triethylamine (2.4 mL, 16.9 mmol) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 68 hours. The mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate. The solution was washed with 1.0 N aqueous sodium hydroxide, then with water, then with saturated aqueous sodium chloride, and the organic phase was dried (sodium sulfate) and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 30% hexane in ethyl acetate, then with 25% hexane in ethyl acetate, to provide a white amorphous solid (3.19 g, 90%). 1H NMR (300 MHz, CDCl3) δ7.84 (s, 1H), 7.65 (d, J=8 Hz, 1H), 7.40 (t, J=8 Hz, 1H), 7.29 (d, J=7 Hz, 1H), 4.20 (s, 3H), 3.85 (m, 1H), 3.75 (m, 1H), 3.28 (dd, J=14, 5 Hz, 1H), 3.05 (m, 2H), 2.81 (dd, J=13, 9 Hz, 1H), 1.9-1.6 (m, 3H), 1.45 (s+m, 10H), 1.27 (m, 1H). Mass spec (AP+) m/z 416.2 (M+H+, 100%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 1.0 N aqueous sodium hydroxide
  4. dry with materialwith water, then with saturated aqueous sodium chloride, and the organic phase was dried (sodium sulfate)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluting with 30% hexane in ethyl acetate

Sources & evidence

ORD record
ord-e398fe01c7c94509b8b7cce54e32f927
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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