Triethylamine → 4-amino-N-(oxan-4-yl)benzamide

HRID 1676517

Reaction equation

HRID 1676517 reaction equation
N1(O[C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)C2C=CC=CC=2N=N1.[NH2:20][C:21]1[CH:26]=[CH:25][O:24][CH2:23][CH:22]=1.C(N(CC)CC)C>CN(C)C=O>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:19])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177912712H-pyran-4-amineHCID 538445834-Amino-benzoic acid benzotriazol-1-yl ester

Product 1

HCID 436095624-amino-N-(oxan-4-yl)benzamideYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.1441 g (4.5 mmole) of 4-amino-benzoic acid benzotriazol-1-yl ester and 8 mL of dry dimethylformamide was added 0.6575 g (6.5 mmole) of 4-amino-pyran followed by 0.4554 g (0.45 mmole) of triethylamine. The mixture stirred at room temperature for 90 minutes. Volatiles were removed under reduced pressure and the residue taken up in ethyl acetate, and the organic layer washed once with 100 mL of 0.5 M sodium carbonate, twice with 75 mL water, and then 75 mL brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.5378 g 4-amino-N-(tetrahydro-pyran-4-yl)-benzamide, which was used without further purification.

Workup

  1. customVolatiles were removed under reduced pressure
  2. washthe organic layer washed once with 100 mL of 0.5 M sodium carbonate, twice with 75 mL water
  3. dry with material75 mL brine, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f59a4f26f1b94892b120d6cb87f857fc
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Linked notes

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