Benzoyl chloride → N-(5,6-Diethyl-indan-2-yl)-benzamide

HRID 2089077Notes

Reaction equation

HRID 2089077 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH2:14])[CH2:6]2)[CH3:2].C(N(CC)CC)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[CH2:12]([C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[CH2:1][CH3:2])[CH2:6][CH:7]([NH:14][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:8]2)[CH3:13]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 101926155,6-diethyl-2,3-dihydro-1H-inden-2-amine

Product 1

HCID 22499179N-(5,6-Diethyl-indan-2-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6-Diethyl-indan-2-ylamine (4.10 g) is dissolved in dichloromethane (DCM) (150 mL) and triethylamine (2.41 g) is added. Benzoyl chloride (3.20 g) is then added dropwise and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by TLC after 1 hour. The solution is washed with 0.2M HCl (100 mL), water (100 mL) and brine (100 mL). The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. Crystallised from ethyl acetate. TLC (silica, dichloromethane/methanol 10:1 Rf=0.85).

Workup

  1. washThe solution is washed with 0.2M HCl (100 mL), water (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. customCrystallised from ethyl acetate

Sources & evidence

ORD record
ord-98015f20010c4e3aaa0e47c775c0cf85
Source dataset
uspto-grants-2013_05
Patent number
US08436017B2

Reaction notes

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