Benzoyl chloride → 6-Benzoyl-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid 2,4-dichloro-benzylamide

HRID 2407531Notes

Reaction equation

HRID 2407531 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:11][C:10]2([CH2:14][NH:13][CH2:12]2)[CH2:9]1)=[O:7].C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:11][C:10]2([CH2:14][N:13]([C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:12]2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 866823442,6-Diaza-spiro[3.3]heptane-2-carboxylic acid 2,4-dichloro-benzylamide

Product 1

HCID 715548976-Benzoyl-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid 2,4-dichloro-benzylamideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Diaza-spiro[3.3]heptane-2-carboxylic acid 2,4-dichloro-benzylamide (245 mg, 416 μmol) and triethylamine (200 mg, 198 mmol) were dissolved in dichloromethane (5 mL) followed by benzoyl chloride (70 mg, 499 μmol) and the reaction mixture was stirred for 1 h at ambient temperature. The crude reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography (SiO2; methanol:dichloromethane 0:1 to 1:19) to give the title compound (106 mg, 63%) as a colorless solid. MS (EI) m/e: 404.1 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by chromatography (SiO2; methanol:dichloromethane 0:1 to 1:19)

Sources & evidence

ORD record
ord-42c5338f76984f34861e54a5ccc3c5bb
Source dataset
uspto-grants-2014_08
Patent number
US08809552B2

Reaction notes

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