Triethylamine → 4-amino-N-(1-ethyl-4-piperidyl)-3-methoxy-benzamide

HRID 1676524Notes

Reaction equation

HRID 1676524 reaction equation
N1(O[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:19][CH3:20])[CH:13]=2)C2C=CC=CC=2N=N1.CS([N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)(=O)=O.[CH2:33](N(CC)CC)[CH3:34]>O1CCCC1>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:32][CH:29]2[CH2:30][CH2:31][N:26]([CH2:33][CH3:34])[CH2:27][CH2:28]2)=[O:21])=[CH:13][C:14]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl esterHCID 113558261-(Methanesulfonyl)piperidin-4-amine

Product 1

HCID 580150934-amino-N-(1-ethyl-4-piperidyl)-3-methoxy-benzamideYield 117%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.8813 g (3.1 mmole) of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester and 8 mL of dry tetrahydrofuran at 0 degrees was added 0.6995 g (3.1 mmole) of 1-methanesulfonyl-piperidin-4-ylamine followed by 0.7842 g (7.75 mmole) of triethylamine. The cooling bath was removed and the mixture stirred at room temperature for 90 hours. Volatiles were removed under reduced pressure and the residue taken up in ethyl acetate, and the organic layer washed twice with 50 mL of 0.5 M sodium carbonate, 50 mL water, and then 50 mL brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1.0056 g 4-amino-N-(1-ethyl-piperidin-4-yl)-3-methoxy-benzamide.

Workup

  1. customThe cooling bath was removed
  2. customVolatiles were removed under reduced pressure
  3. washthe organic layer washed twice with 50 mL of 0.5 M sodium carbonate, 50 mL water
  4. dry with material50 mL brine, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f120b2c81d5248e887e32a0bfa2673a4
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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