Triethylamine → N-(1-benzyl-piperidin-4-yl)-2-methoxy-6-nitrobenzamide

HRID 2250254Notes

Reaction equation

HRID 2250254 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:4]=1[C:5]([OH:7])=O.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:22]([N:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:5](=[O:7])[C:4]2[C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[CH2:17][CH2:18]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 4158521-Benzyl-4-piperidylamineHCID 133000352-Methoxy-6-nitrobenzoic acid

Product 1

HCID 21102223N-(1-benzyl-piperidin-4-yl)-2-methoxy-6-nitrobenzamideYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

2-Methoxy-6-nitro-benzoic acid (2.0 g, 10.1 mmol), 4-amino-1-benzylpiperidine (1.9 mL, 10.1 mmol), 1-hydroxybenzotriazole (1.43 g, 10.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (1.9 g, 10.1 mmol) were combined in ethyl acetate (25 mL). To this solution was added triethylamine (4.2 mL. 30.3 mmol) and the reaction mixture stirred at 40° C. for 2 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water (2×), 5% sodium bicarbonate, brine (2×), dried over sodium sulfate, and concentrated to afford 3.2 g (86%) of the desired product. LC/MS: tR=1.10 min, 370.28 (MH)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (2×), 5% sodium bicarbonate, brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ba388aeb3e60407592aa1d11768b4d3b
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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